Electroluminescent metal complexes with nucleophilic carbene ligands

ABSTRACT

This invention relates to electroluminescent metal complexes of the formula (I), wherein the ring A, formula (II), represents an optionally substituted aryl group which can optionally contain heteroatoms, the ring B, formula (III), represents an optionally substituted nitrogen containing aryl group, which can optionally contain further heteroatoms, or the ring A may be taken with the ring B binding to the ring A to form a ring; the group C, formula (IV), represents an acyclic carbene, or a cyclic carbene (ring C), which can optionally contain heteroatoms, the ring D, formula (V), represents an optionally substituted aryl group which can optionally contain heteroatoms, n1 is an integer of 1 to 3, m1 is an integer of 0, 1, or 2, m2 is an integer 0, or 1, M 1  is a metal with an atomic weight of greater than 40, L 3  is a monodentate ligand, or a bidentate ligand, Y is —C(═O)—, or —C(X 1 ) 2- , wherein X 1  is hydrogen, or C 1-4 alkyl, especially hydrogen, and y is 0, or 1, especially 0; a process for their preparation, electronic devices comprising the metal complexes and their use in electronic devices, especially organic light emitting diodes (OLEDs), as oxygen sensitive indicators, as phosphorescent indicators in bioassays, and as catalysts.

This invention relates to electroluminescent metal complexes withnucleophilic carbene ligands, a process for their preparation,electronic devices comprising the metal complexes and their use inelectronic devices, especially organic light emitting diodes (OLEDs), asoxygen sensitive indicators, as phosphorescent indicators in bioassays,and as catalysts.

Organic electronic devices that emit light, such as light-emittingdiodes that make up displays, are present in many different kinds ofelectronic equipment. In all such devices, an organic active layer issandwiched between two electrical contact layers. At least one of theelectrical contact layers is light-transmitting so that light can passthrough the electrical contact layer. The organic active layer emitslight through the light-transmitting electrical contact layer uponapplication of electricity across the electrical contact layers. It iswell known to use organic electroluminescent compounds as the activecomponent in light-emitting diodes. Simple organic molecules such asanthracene, thiadiazole derivatives, and coumarin derivatives are knownto show electroluminescence. Semiconductive conjugated polymers havealso been used as electroluminescent components, as has been disclosedin, for example, in U.S. Pat. Nos. 5,247,190, 5,408,109 and EP-A-443861. Complexes of 8-hydroxyquinolate with trivalent metal ions,particularly aluminum, have been extensively used as electroluminescentcomponents, as has been disclosed in, for example, U.S. Pat. No.5,552,678. Burrows and Thompson have reported thatfac-tris(2-phenylpyridine) iridium can be used as the active componentin organic light-emitting devices. (Appl. Phys. Lett. 1999, 75, 4.) Theperformance is maximized when the iridium compound is present in a hostconductive material. Thompson has further reported devices in which theactive layer is poly(N-vinyl carbazole) doped withfac-tris[2-(4′,5′-difluorophenyl)pyridine-C′₂,N]iridium(III). (PolymerPreprints 2000, 41(1), 770.)

P. B. Hitchcock et al., J. Organometallic Chemistry 239 (1982) C26-C30,describe the preparation of the Ir complexes of the formula

Hiraki et al., J. Organomet. Chem. 1981, 413 bis 419 describe thepreparation and the characterization of the following carbene complexes:

Danapoulos et al., J. Chem. Soc., Dalton Trans. (2002) 3090 bis 3091describe the preparation of the following carbene complex:

wherein L-L=η⁴-1,5-cyclooctadiene; Ar=2,6-diisopropylphenyl.

There is, however, a continuing need for electroluminescent compoundswith excellent light emitting characteristics and durability.

Accordingly the present invention is directed to compounds (metalcomplexes) of the formula

wherein

the ring A,

represents an optionally substituted aryl group which can optionallycontain heteroatoms,

the ring B,

represents an optionally substituted nitrogen containing aryl group,which can optionally contain further heteroatoms, or the ring A may betaken with the ring B binding to the ring A to form a ring;

the group C,

represents an acyclic carbene, or a cyclic carbene (ring C), which canoptionally contain heteroatoms,

the ring D,

represents an optionally substituted aryl group which can optionallycontain heteroatoms,

n1 is an integer of 1 to 3,

m1 is an integer of 0, 1, or 2,

m2 is an integer 0, or 1,

M¹ is a metal with an atomic weight of greater than 40,

L³ is a monodentate ligand, or a bidentate ligand,

Y is —C(═O)—, or —C(X¹)₂-, wherein X¹ is hydrogen, or C₁₋₄alkyl,especially hydrogen, and

y is 0, or 1, especially 0; with the proviso that the followingcompounds

wherein L-L=η⁴-1,5-cyclooctadiene; Ar=2,6-diisopropylphenyl, areexcluded; a process for their preparation, electronic devices comprisingthe metal complexes and their use in electronic devices, especiallyorganic light emitting diodes (OLEDs), as oxygen sensitive indicators,as phosphorescent indicators in bioassays, and as catalysts.

The metal complexes of the present invention are characterized in thatat least one ligand is derived from a nucleophilic carbene.

The metal is generally a metal M¹ with an atomic weight of greater than40, Preferably the metal M¹ is selected from Tl, Pb, Bi, In, Sn, Sb, Te,especially Mo, Cr, Mn, Ta, V, Cu, Fe, Ru, Ni, Co, Ir, Pt, Pd, Rh, Re,Os, Ag and Au. More preferably the metal is selected from Ir and Ru aswell as Ag, Au, Pt and Pd, wherein Ir and Pt are most preferred.

“Nucleophilic carbene ligand” in the context of the present inventionmeans typical σ-donor ligands that can substitute classical 2e⁻ donorligands. They can be cyclic or acyclic. They can have no or severaldifferent heteroatoms or several heteroatoms of the same kind. Possiblecarbenes are, for example, diarylcarbenes, cyclic diaminocarbenes,imidazol-2-ylidenes, imidazolidin-2-ylidene, 1,2,4-triazol-3-ylidenes,1,3-thiazol-2-ylidenes, acyclic diaminocarbenes, acyclicaminooxycarbenes, acyclic aminothiocarbenes, cyclic diborylcarbenes,acyclic diborylcarbenes, phosphinosilyl-carbenes,phosphinophosphonio-carbenes, sulfenyl-trifluormethylcarbenes,sulfenylpentafluorothiocarbenes etc.

The term “ligand” is intended to mean a molecule, ion, or atom that isattached to the coordination sphere of a metallic ion. The term“complex”, when used as a noun, is intended to mean a compound having atleast one metallic ion and at least one ligand. The term “group” isintended to mean a part of a compound, such a substituent in an organiccompound or a ligand in a complex. The term “facial” is intended to meanone isomer of a complex, Ma₃b₃, having octahedral geometry, in which thethree “a” groups are all adjacent, i.e. at the corners of one triangularface of the octahedron. The term “meridional” is intended to mean oneisomer of a complex, Ma₃b₃, having octahedral geometry, in which thethree “a” groups occupy three positions such that two are trans to eachother, i.e. the three “a” groups sit in three coplanar positions,forming an arc across the coordination sphere that can be thought of asa meridion. The phrase “adjacent to,” when used to refer to layers in adevice, does not necessarily mean that one layer is immediately next toanother layer. The term “photoactive” refers to any material thatexhibits electroluminescence and/or photosensitivity.

If M¹ is Co, or Fe, especially Ir, or Rh, n1 is preferably 3, morepreferably 1.

If M¹ is Ni, Rh, or Ru, especially Pd, or Pt, n1 is preferably 2, morepreferably 1.

In an embodiment of the present invention compounds of formula I arepreferred, wherein M¹ is Co, or Fe, especially Ir, or Rh, m2 is 0, n1 is1 and m1 is 2.

In another embodiment of the present invention compounds of formula Iare preferred, wherein M¹ is Ni, Rh, or Ru, especially Pd, or Pt, m2 is0, n1 is 1 and m1 is 1.

If the group

represents an acyclic nucleophilic carbene it is preferably a group ofthe following formula

wherein X═Y═N, B, or P;

wherein X¹ is N, or P and Y¹ is S, or O; >SiX²X³, or >CZ⁵Z³, wherein X²and X³ are independently of each other C₁-C₄alkyl and R⁵, Z³, Z⁴, Z⁵ andZ⁶ are as defined below.

y is 0, or 1, especially 0. The ring D,

is preferably a group of formula

wherein R¹ to R⁴ are substitutents and can be taken together to form aring.

Examples that specify the possibilities for the group designated aboveare as follows:

Cyclic carbenes,

(ring C), are preferred against acyclic carbenes. Examples of a ring Care as follows:

especially

wherein

R⁵ is a substitutent, such as hydrogen, C₁-C₂₄alkyl, C₂-C₂₄alkenyl,C₂-C₂₄alkynyl, C₂-C₂₄alkoxycarbonyl, C₁-C₂₄carboxylate, C₁-C₂₄alkoxy,C₂-C₂₄alkenyloxy, C₂-C₂₄alkynyloxy, or aryloxy, which can optionally besubstituted with C₁-C₈alkyl, halogen, C₁-C₈alkoxy, or with a phenylgroup, which can be substituted with halogen, C₁-C₈alkyl, orC₁-C₈alkoxy, especially aryl, which can optionally be substituted; and

R⁶, Z¹, Z², Z³, Z⁴, Z⁵ and Z⁶ are independently of each other selectedfrom the group consisting of hydrogen, C₁-C₂₄alkyl, C₁-C₂₄halogenalkyl,especially C₁-C₈perfluoroalkyl, C₂-C₂₄alkenyl, C₂-C₂₄alkynyl,C₂-C₂₄alkoxycarbonyl, aryl, which can optionally be substituted,C₁-C₂₄carboxylate, C₁-C₂₄alkoxy, C₂-C₂₄alkenyloxy, C₂-C₂₄alkynyloxy, oraryloxy, wherein each of Z¹, Z², Z³ and Z⁴ optionally being substitutedwith C₁-C₈alkyl, halogen, C₁-C₈alkoxy, or with a phenyl group, which canoptionally be substituted with halogen, C₁-C₈alkyl, or C₁-C₈alkoxy, or

Z¹ and Z², if possible, form an aromatic or heteroaromatic ring, and/or

Z³, Z⁴, Z⁵ and Z⁶, if possible, form an alkyl or heteroalkyl ring.

In one embodiment cyclic carbenes,

(ring C), are preferred, wherein ring C is represented by the followingformula:

In another embodiment cyclic carbenes,

(ring C), are preferred, wherein ring C is represented by the followingformula:

In said embodiment the ligand

(L¹) is preferably a group of formula

wherein

R¹ to R⁴ are substitutents and can be taken together to form a ring,

y is 0, or 1, especially 0, the group C,

is a group (nucleophilic carbene) of the following formula

especially

very especially

wherein

R⁵ is a substitutent, especially hydrogen, C₁-C₂₄alkyl, C₂-C₂₄alkenyl,C₂-C₂₄alkynyl, C₂-C₂₄alkoxycarbonyl, C₁-C₂₄carboxylate, C₁-C₂₄alkoxy,C₂-C₂₄alkenyloxy, C₂-C₂₄alkynyloxy, or aryloxy, which can optionally besubstituted with C₁-C₈alkyl, halogen, C₁-C₈alkoxy, or with a phenylgroup, which can be substituted with halogen, C₁-C₈alkyl, orC₁-C₈alkoxy, especially aryl, which can optionally be substituted; and

Z¹, Z², Z³, Z⁴, Z⁵ and Z⁶ are independently of each other selected fromthe group consisting of hydrogen, C₁-C₂₄alkyl, C₁-C₂₄halogenalkyl,especially C₁-C₈perfluoroalkyl, C₂-C₂₄alkenyl, C₂-C₂₄alkynyl,C₂-C₂₄alkoxycarbonyl, aryl, which can optionally be substituted,C₁-C₂₄carboxylate, C₁-C₂₄alkoxy, C₂-C₂₄alkenyloxy, C₂-C₂₄alkynyloxy, oraryloxy, wherein each of Z¹, Z², Z³ and Z⁴ optionally being substitutedwith C₁-C₈alkyl, halogen, C₁-C₈alkoxy, or with a phenyl group, which canoptionally be substituted with halogen, C₁-C₈alkyl, or C₁-C₈alkoxy, or

Z¹ and Z², if possible, form an aromatic or heteroaromatic ring, and/or

Z³, Z⁴, Z⁵ and Z⁶, if possible, form an alkyl or heteroalkyl ring.

R¹, R², R³ and R⁴ are independently of each other hydrogen, halogen,especially F, or Cl; nitro, cyano, C₁-C₄alkyl, C₁-C₄perfluoroalkyl, orC₁-C₄alkoxy, —S—C₁-C₄alkyl, —O—C₁-C₄perfluoroalkyl, —SO₂X²², —CO₂H,—CO₂X²², wherein X²² is C₁-C₄alkyl; C₆H₄CF₃, cyclohexyl, optionallysubstituted C₆-C₁₀aryl, especially phenyl, optionally substituted—O—CH₂—C₆-C₁₀aryl, especially benzyloxy, or optionally substituted—O—C₆-C₁₀aryl, especially phenoxy.

R¹ is preferably hydrogen, halogen, especially F, or Cl; nitro, cyano,C₁-C₄alkyl, C₁-C₄perfluoroalkyl, or C₁-C₄alkoxy.

R² is preferably hydrogen, halogen, especially F, or Cl; nitro, cyano,C₁-C₄alkyl, C₁-C₄perfluoroalkyl, C₁-C₄alkoxy, —O—C₁-C₄perfluoroalkyl,—SO₂X²², —CO₂X²², wherein X²² is C₁-C₄alkyl; C₆H₄CF₃, or optionallysubstituted —O—C₆-C₁₀aryl, especially phenoxy.

R³ is preferably hydrogen, halogen, especially F, or Cl; nitro, cyano,C₁-C₄alkyl, C₁-C₄perfluoroalkyl, C₁-C₄alkoxy, —S—C₁-C₄alkyl, or—O—C₁-C₄perfluoroalkyl.

R⁴ is preferably hydrogen, halogen, especially F, or Cl.

According to the present invention the metal complexes comprise at leasta nucleophilic carbene ligand, i.e. it may comprise two or three (ormore) nucleophilic carbene ligands (L¹).

Especially preferred examples of ring C are

wherein R⁵, Z¹, Z², Z³, and Z⁴ are as defined above. R⁵ is preferablyoptionally substituted C₆-C₁₀aryl, especially phenyl. Z¹ is preferablyC₁-C₄perfluoroalkyl, or optionally substituted C₆-C₁₀aryl, especiallyphenyl. In a preferred embodiment R⁵ is optionally substitutedC₆-C₁₀aryl, especially phenyl and Z¹ is C₁-C₄perfluoroalkyl.

An optionally substituted C₆-C₁₀aryl group is especially a phenyl group,which is substituted by one or more C₁-C₄alkyl groups,C₁-C₄perfluoroalkyl groups and/or fluorine atoms.

Examples of a group of formula

Examples of a group of formula

wherein X can be O, or S are

Especially preferred examples of ligands L¹ are

wherein

R¹ is hydrogen, halogen, especially F, or Cl; nitro, cyano, C₁-C₄alkyl,C₁-C₄perfluoroalkyl, or C_(i)-C₄alkoxy,

R² is hydrogen, halogen, especially F, or Cl; nitro, cyano, C₁-C₄alkyl,C₁-C₄perfluoroalkyl, C₁-C₄alkoxy, —S—C₁-C₄alkyl, —O—C₁-C₄perfluoroalkyl,—SO₂X²², —CO₂X²², wherein X²² is C₁-C₄alkyl; C₆H₄CF₃, or optionallysubstituted —O—C₆-C₁₀aryl, especially phenoxy,

R³ is hydrogen, halogen, especially F, or Cl; nitro, cyano, C₁-C₄alkyl,C₁-C₄perfluoroalkyl, C₁-C₄alkoxy, —S—C₁-C₄alkyl, or—O—C₁-C₄perfluoroalkyl,

R⁴ is hydrogen, halogen, especially F, or Cl;

R⁵ is optionally substituted C₆-C₁₀aryl, C₁-C₄alkyl,C₁-C₄perfluoroalkyl, C₁-C₄alkoxy, or —O—C₁-C₄perfluoroalkyl, especiallyphenyl, and

Z¹ is C₁-C₄perfluoroalkyl, or optionally substituted C₆-C₁₀aryl,especially phenyl.

In a further embodiment the present invention is directed to metalcomplexes comprising at least one ligand derived from a nucleophiliccarbene (L¹) and at least one ligand of formula

(L²).

The preferred ring B includes a phenyl group, a substituted phenylgroup, a naphthyl group, a substituted naphthyl group, a furyl group, asubstituted furyl group, a benzofuryl group, a substituted benzofurylgroup, a thienyl group, a substituted thienyl group, a benzothienylgroup, a substituted benzothienyl group, and the like. The substitutenton the substituted phenyl group, substituted naphthyl group, substitutedfuryl group, substituted benzofuryl group, substituted thienyl group,and substituted benzothienyl group include C₁-C₂₄alkyl groups,C₂-C₂₄alkenyl groups, C₂-C₂₄alkynyl groups, aryl groups, heteroarylgroups, C₁-C₂₄alkoxy groups, C₁-C₂₄alkylthio groups, a cyano group,C₂-C₂₄acyl groups, C₁-C₂₄alkyloxycarbonyl groups, a nitro group, halogenatoms, alkylenedioxy groups, and the like.

In said embodiment the ligand

(L²) is preferably a group of formula

wherein R⁶, R⁷, R⁸, and R⁹ are independently of each other hydrogen,C₁-C₂₄alkyl, C₂-C₂₄alkenyl, C₂-C₂₄alkynyl, aryl, heteroaryl,C₁-C₂₄alkoxy, C₁-C₂₄alkylthio, cyano, acyl, alkyloxycarbonyl, a nitrogroup, or a halogen atom; or two substituents R⁶, R⁷, R⁸, and R⁹, whichare adjacent to each other, together form a group

wherein R²⁰⁵, R²⁰⁶, R²⁰⁷ and R²⁰⁸ m are independently of each other H,or C₁-C₈alkyl,

the ring A represents an optionally substituted aryl or heteroarylgroup; or the ring A may be taken with the pyridyl group binding to thering A to form a ring; the alkyl group, alkenyl group, alkynyl group,aryl group, heteroaryl group, alkoxy group, alkylthio group, acyl group,and alkyloxycarbonyl group represented by R⁶, R⁷, R⁸, and R⁹ may besubstituted.

An example of a preferred class of ligands L² are compounds of theformula

especially

wherein Y is S, O, NR²⁰⁰, wherein R²⁰⁰ is hydrogen, cyano, C₁-C₄alkyl,C₂-C₄alkenyl, optionally substituted C₆-C₁ aryl, especially phenyl,—(CH₂)_(r)—Ar, wherein Ar is an optionally substituted C₆-C₁₀aryl,especially

a group —(CH₂)_(r)X²⁰, wherein r′ is an integer of 1 to 5, X²⁰ ishalogen, especially F, or Cl; hydroxy, cyano, —O—C₁-C₄alkyl,di(C₁-C₄alkyl)amino, amino, or cyano; a group —(CH₂)_(r)OC(O)(CH₂)r″CH₃,wherein r is 1, or 2, and r″ is 0, or 1;

—NH-Ph, —C(O)CH₃, —CH₂—O—(CH₂)₂—Si(CH₃)₃, or

Another preferred class of ligands L² is described in European patentapplication 04102981.0, of which the following can advantageously beused according to the present invention:

wherein

Q¹ and Q² are independently of each other hydrogen, C₁-C₂₄alkyl, orC₆-C₁₈aryl, A²¹ is hydrogen,

A²² is hydrogen, or C₆-C₁₀aryl,

A²³ is hydrogen, or C₆-C₁₀aryl,

A²⁴ is hydrogen, or

A²³ and A²⁴, or A²³ and A²⁴ together form a group

wherein R²⁰⁵, R²⁰⁶, R²⁰⁷ and

R²⁰⁸ are independently of each other H, or C₁-C₈alkyl,

R⁴² is H, F, C₁-C₄alkyl, C₁-C₈alkoxy, or C₁-C₄perfluoroalkyl,

R⁴³ is H, F, C₁-C₄alkyl, C₁-C₈alkoxy, C₁-C₄perfluoroalkyl, orC₆-C₁₀aryl,

R⁴⁴ is H, F, C₁-C₄alkyl, C₁-C₈alkoxy, or C₁-C₄perfluoroalkyl, and

R⁴⁵ is H, F, C₁-C₄alkyl, C₁-C₈alkoxy, or C₁-C₄perfluoroalkyl.

Another preferred class of ligands L² is a compound of formula

wherein R⁶ is hydrogen, halogen, especially F, or Cl; nitro, C₁-C₄alkyl,C₁-C₄perfluoroalkyl, C₁-C₄alkoxy, or optionally substituted C₆-C₁₀aryl,especially phenyl,

R⁷ is hydrogen, halogen, especially F, or Cl; C₁-C₄alkyl,C₁-C₄perfluoroalkyl, optionally substituted C₆-C₁₀aryl, especiallyphenyl, or optionally substituted C₆-C₁₀perfluoroaryl, especially C₆F₅,

R⁸ is hydrogen, C₁-C₄alkyl, C₁-C₈alkoxy, C₁-C₄perfluoroalkyl, optionallysubstituted C₆-C₁₀aryl, especially phenyl, or optionally substitutedC₆-C₁₀perfluoroaryl, especially C₆F₅,

R⁹ is hydrogen, halogen, especially F, or Cl; nitro, cyano, C₁-C₄alkyl,C₁-C₄perfluoroalkyl, C₁-C₄alkoxy, or optionally substituted C₆-C₁₀aryl,especially phenyl,

A¹⁰ is hydrogen, halogen, especially F, or Cl; nitro, cyano, C₁-C₄alkyl,C₂-C₄alkenyl, C₁-C₄perfluoroalkyl, —O—C₁-C₄perfluoroalkyl,tri(C₁-C₄alkyl)silanyl, especially tri(methyl)silanyl, optionallysubstituted C₆-C₁₀aryl, especially phenyl, or optionally substitutedC₆-C₁₀perfluoroaryl, especially C₆F₅,

A¹¹ is hydrogen, halogen, especially F, or Cl; nitro, cyano, C₁-C₄alkyl,C₂-C₄alkenyl, C₁-C₄perfluoroalkyl, —O—C₁-C₄perfluoroalkyl,tri(C₁-C₄alkyl)silanyl, especially tri(methyl)silanyl, optionallysubstituted C₆-C₁₀aryl, especially phenyl, or optionally substitutedC₆-C₁₀perfluoroaryl, especially C₆F₅,

A¹² is hydrogen, halogen, especially F, or Cl; nitro, hydroxy, mercapto,amino, C₁-C₄alkyl, C₂-C₄alkenyl, C₁-C₄perfluoroalkyl, C₁-C₄alkoxy,—O—C₁-C₄perfluoroalkyl, —S—C₁-C₄alkyl, a group —(CH₂)_(r)X²⁰, wherein ris 1, or 2, X²⁰ is halogen, especially F, or Cl; hydroxy, cyano,—O—C₁-C₄alkyl, di(C₁-C₄alkyl)amino, —CO₂X²¹, wherein X²¹ is H, orC₁-C₄alkyl; —CH═CHCO₂X²², wherein X²² is C₁-C₄alkyl; —CH(O), —SO₂X²³,—SOX²³, —NC(O)X²³, —NSO₂X²³, —NHX²³, —N(X²³)₂, wherein X²³ isC₁-C₄alkyl; tri(C₁-C₄alkyl)siloxanyl, optionally substituted—O—C₆-C₁₀aryl, especially phenoxy, cyclohexyl, optionally substitutedC₆-C₁₀aryl, especially phenyl, or optionally substitutedC₆-C₁₀perfluoroaryl, especially C₆F₅, and

A¹³ is hydrogen, nitro, cyano, C₁-C₄alkyl, C₂-C₄alkenyl,C₁-C₄perfluoroalkyl, —O—C₁-C₄perfluoroalkyl, tri(C₁-C₄alkyl)silanyl, oroptionally substituted C₆-C₁₀aryl.

Specific examples of L² are the following compounds (VI-1) to (VI-53):

Special emphasis among them is given to (VI-1) to (VI-47).

The ligand L³ is preferably a (monoanionic) bidentate ligand. In generalthese ligands have N, O, P, or S as coordinating atoms and form 5- or 6-membered rings when coordinated to the iridium. Suitable coordinatinggroups include amino, imino, amido, alkoxide, carboxylate, phosphino,thiolate, and the like. Examples of suitable parent compounds for theseligands include β-dicarbonyls (β-enolate ligands), and their N and Sanalogs; amino carboxylic acids(aminocarboxylate ligands); pyridinecarboxylic acids (iminocarboxylate ligands); salicylic acid derivatives(salicylate ligands); hydroxyquinolines (hydroxyquinolinate ligands) andtheir S analogs; and diarylphosphinoalkanols (diarylphosphinoalkoxideligands).

Examples of bidentate ligands L³ are

wherein

R¹¹ and R¹⁵ are independently of each other hydrogen, C₁-C₈alkyl,C₆-C₁₈aryl, C₂-C₁₀heteroaryl, or C₁-C₈perfluoroalkyl,

R¹² and R¹⁶ are independently of each other hydrogen, or C₁-C₈alkyl, and

R¹³ and R¹⁷ are independently of each other hydrogen, C₁-C₈alkyl,C₆-C₁₈aryl, C₂-C₁₀heteroaryl, C₁-C₈perfluoroalkyl, or C₁-C₈alkoxy, and

R¹⁴ is C₁-C₈alkyl, C₆-C₁₀aryl, C₇-C₁₁aralkyl, or C₁-C₈alkoxy,

R¹⁸ is C₆-C₁₀aryl,

R¹⁹ is C₁-C₈alkyl,

R²⁰ is C₁-C₈alkyl, or C₆-C₁₀aryl,

R²¹ is hydrogen, C₁-C₈alkyl, or C₁-C₈alkoxy, which may be partially orfully fluorinated,

R²² and R²³ are independently of each other C_(n)(H+F)_(2n+1), orC₆(H+F)₅,

R²⁴ can be the same or different at each occurrence and is selected fromH, or C_(n)H+F)_(2n+1),

p is 2, or 3, and

R⁴⁶ is C₁-C₈alkyl, C₆-C₁₈aryl, or C₆-C₁₈aryl, which is substituted byC₁-C₈alkyl.

Examples of suitable phosphino alkoxide ligands

(WO03040256) are listed below:

3-(diphenylphosphino)-1-oxypropane [dppO]

1,1-bis(trifluoromethyl)-2-(diphenylphosphino)-ethoxide [tfmdpeO].

Examples of particularly suitable compounds HL³,

from which the ligands L³ are derived, include

The hydroxyquinoline parent compounds, HL³, can be substituted withgroups such as alkyl or alkoxy groups which may be partially or fullyfluorinated.

8-hydroxyquinaldine, 7-N-propyl-8-hydroxyquinoline,5,7-dimethyl-8-hydroxyquinoline, 2-phenyl-quinolin-8-ol,8-hydroxy-3-methylquinoline, 4-acridinol,5,7-dibromo-8-hydroxyquinoline, 5,7-dichloro-8-hydroxyquinoline,5-chloro-8-hydroxy-7-iodoquinoline, 5-chloro-8-hydroxyquinoline,5,7-diiodo-8-hydroxyquinoline, 7-bromo-5-chloro-8-hydroxyquinoline,5-fluoro-8-hydroxyquinoline, 2,5,7-trichloro-quinolin-8-ol,5-hydroxymethyl-quinolin-8-ol, quinoline-2,8-diol,5-nitro-quinolin-8-ol, 6-nitro-quinolin-8-ol 5-amino-8-hydroxyquinolinedihydrochloride, 5-nitroso-quinolin-8-ol, 2-amino-quinolin-8-ol,2-(butyl-quinolin-2-yl-amino)-quinolin-8-ol,7-piperidin-1-ylmethyl-quinolin-8-ol,5-chloro-7-morpholin-4-ylmethyl-quinolin-8-ol,8-hydroxy-5-nitro-quinoline-2-carbaldehyde,8-hydroxy-quinoline-5-carbaldehyde,8-hydroxy-5,7-dimethyl-quinoline-2-carbaldehyde,8-hydroxy-quinoline-2-carbaldehyde, 8-hydroxy-quinoline-2-carbonitrile,2-hydrazino-5,7-dimethyl-quinolin-8-ol, 5-octyloxymethyl-quinolin-8-ol,5-(chloromethyl)-8-quinolinol hydrochloride,2-[(E)-2-(5-bromo-thiophen-2-yl)-vinyl]-quinolin-8-ol,2-[(E)-2-(2-bromo-phenyl)-vinyl]-quinolin-8-ol, and2-[(E)-2-(2-amino-phenyl)-vinyl]-quinolin-8-ol.

In general, these compounds are commercially available. Examples ofespecially suitable hydroxyquinolinate ligands, L³, include:

8-hydroxyquinolinate [8hq]

2-methyl-8-hydroxyquinolinate [Me-8hq]

10-hydroxybenzoquinolinate [10-hbq].

In a preferred embodiment of the present invention the metal complex offormula I is a compound of formula

wherein

M¹ is Co, or Fe, especially Ir, or Rh,

R¹, R², R³ and R⁴ are hydrogen, or halogen, especially F, or Cl;

R⁵ is optionally substituted C₆-C₁₀aryl, C₁-C₄alkyl,C₁-C₄perfluoroalkyl, C₁-C₄alkoxy, or —O—C₁-C₄perfluoroalkyl, especiallyphenyl,

R⁶ is hydrogen, halogen, especially F, or Cl; nitro, C₁-C₄alkyl,C₁-C₄perfluoroalkyl, C₁-C₄alkoxy, or optionally substituted C₆-C₁₀aryl,especially phenyl,

R⁷ is hydrogen, halogen, especially F, or Cl; C₁-C₄alkyl,C₁-C₄perfluoroalkyl, optionally substituted C₆-C₁₀aryl, especiallyphenyl, or optionally substituted C₆-C₁₀perfluoroaryl, especially C₆F₅,

R⁸ is hydrogen, C₁-C₄alkyl, C₁-C₈alkoxy, C₁-C₄perfluoroalkyl, optionallysubstituted C₆-C₁₀aryl, especially phenyl, or optionally substitutedC₆-C₁₀perfluoroaryl, especially C₆F₅,

R⁹ is hydrogen, halogen, especially F, or Cl; nitro, cyano, C₁-C₄alkyl,C₁-C₄perfluoroalkyl, C₁-C₄alkoxy, or optionally substituted C₆-C₁₀aryl,especially phenyl,

A¹⁰ is hydrogen, halogen, especially F, or Cl; nitro, cyano, C₁-C₄alkyl,C₂-C₄alkenyl, C₁-C₄perfluoroalkyl, —O—C₁-C₄perfluoroalkyl,tri(C₁-C₄alkyl)silanyl, especially tri(methyl)silanyl, optionallysubstituted C₆-C₁₀aryl, especially phenyl, or optionally substitutedC₆-C₁₀perfluoroaryl, especially C₆F₅,

A¹¹ is hydrogen, halogen, especially F, or Cl; nitro, cyano, C₁-C₄alkyl,C₂-C₄alkenyl, C₁-C₄perfluoroalkyl, —O—C₁-C₄perfluoroalkyl,tri(C₁-C₄alkyl)silanyl, especially tri(methyl)silanyl, optionallysubstituted C₆-C₁₀aryl, especially phenyl, or optionally substitutedC₆-C₁₀perfluoroaryl, especially C₆F₅,

A¹² is hydrogen, halogen, especially F, or Cl; nitro, hydroxy, mercapto,amino, C₁-C₄alkyl, C₂-C₄alkenyl, C₁-C₄perfluoroalkyl, C₁-C₄alkoxy,—O—C₁-C₄perfluoroalkyl, —S—C₁-C₄alkyl, a group —(CH₂)_(r)X²⁰, wherein ris 1, or 2, X²⁰ is halogen, especially F, or Cl; hydroxy, cyano,—O—C₁-C₄alkyl, di(C₁-C₄alkyl)amino, —CO₂X²¹, wherein X²¹ is H, orC₁-C₄alkyl; —CH═CHCO₂X²², wherein X²² is C₁-C₄alkyl; —CH(O), —SO₂X²³,—SOX²³, —NC(O)X²³, —NSO₂X²³, —NHX²³, —N(X²³)₂, wherein X²³ isC₁-C₄alkyl; tri(C₁-C₄alkyl)siloxanyl, optionally substituted—O—C₆-C₁₀aryl, especially phenoxy, cyclohexyl, optionally substitutedC₆-C₁₀aryl, especially phenyl, or optionally substitutedC₆-C₁₀perfluoroaryl, especially C₆F₅,

A¹³ is hydrogen, nitro, cyano, C₁-C₄alkyl, C₂-C₄alkenyl,C₁-C₄perfluoroalkyl, —O—C₁-C₄perfluoroalkyl, tri(C₁-C₄alkyl)silanyl, oroptionally substituted C₆-C₁₀aryl, especially phenyl, and Z¹ isC₁-C₄perfluoroalkyl, or optionally substituted C₆-C₁₀aryl, especiallyphenyl.

Examples of specific compounds are compounds A-1 to A-320 and A′-1 toA′-320 (see claim 7). Special emphasis among them is given to compoundsA-1 to A-58 and A-60 to A-79, especially A-1, A-2, A-4 to A-7, A-10,A-12, A-17, A-18, A-23 to A-26, A-32, A-36, A-39, A-40, A-42, A-43,A-45, A-47 to A-50, A-53 to A-55, A-71, A-72, A-77, A-79. Compounds ofspecial industrial importance among them are the compounds of type A aswell as A′, corresponding to the above formulae (Ia) and (Ib) wherein M¹is Ir, of the numbers 1-7, 9, 12, 17-18, 24, 32, 34, 36, 38-40, 42-43,45, 47, 49-50, 53-54, 71-74, 76-77, 80-83, 85-117, 119, 122, 127-128,134, 142, 144, 146, 148-150, 152-153, 155, 157, 159-160, 163-164,181-184, 186-187, 190-193, 195-217, 219, 222, 227-228, 234, 242, 244,246, 248-250, 252-253, 255, 257, 259-260, 263-263, 281-284, 286-287,290-293, 295-320.

Examples for more preferred embodiments include compounds of the aboveformula (Ib) or especially (Ia) wherein R¹, R², R³, R⁴, R⁶ and A¹³ eachare hydrogen;

R⁵ is optionally substituted C₆-C₁₀aryl such as phenyl;

Z¹ is CF₃ or phenyl or substituted phenyl;

R⁷ is hydrogen, F or CF₃;

one of R⁸ and R⁹, especially R⁸, is hydrogen, C₁-C₄alkyl, C₁-C₈alkoxy,and the other is hydrogen; or R⁸ and R⁹, together with the carbon atomsthey are bonding to, form an annellated aromatic, optionallysubstituted, carbocyclic 6-membered ring, an example for R⁸ and R⁹together thus being the divalent moiety —CH═CH—CH═CH—;

and A¹⁰, A¹¹ and A¹² independently are selected from hydrogen, F, CF₃,CN, such as the compounds:

In a preferred embodiment of the present invention the metal complex offormula I is a compound of formula

wherein

M¹ is Co, or Fe, especially Ir, or Rh,

R¹, R², R³ and R⁴ are hydrogen, or halogen, especially F, or Cl;

R⁵ is optionally substituted C₆-C₁₀aryl, C₁-C₄alkyl,C₁-C₄perfluoroalkyl, C₁-C₄alkoxy, or —O—C₁-C₄perfluoroalkyl, especiallyphenyl,

R⁶ is hydrogen, halogen, especially F, or Cl; nitro, C₁-C₄alkyl,C₁-C₄perfluoroalkyl, C₁-C₄alkoxy, or optionally substituted C₆-C₁₀aryl,especially phenyl,

R⁷ is hydrogen, halogen, especially F, or Cl; C₁-C₄alkyl,C₁-C₄perfluoroalkyl, optionally substituted C₆-C₁₀aryl, especiallyphenyl, or optionally substituted C₆-C₁₀perfluoroaryl, especially C₆F₅,

R⁸ is hydrogen, C₁-C₄alkyl, C₁-C₈alkoxy, C₁-C₄perfluoroalkyl, optionallysubstituted C₆-C₁₀aryl, especially phenyl, or optionally substitutedC₆-C₁₀perfluoroaryl, especially C₆F₅,

R⁹ is hydrogen, halogen, especially F, or Cl; nitro, cyano, C₁-C₄alkyl,C₁-C₄perfluoroalkyl, C₁-C₄alkoxy, or optionally substituted C₆-C₁₀aryl,especially phenyl,

A¹⁰ is hydrogen, halogen, especially F, or Cl; nitro, cyano, C₁-C₄alkyl,C₂-C₄alkenyl, C₁-C₄perfluoroalkyl, —O—C₁-C₄perfluoroalkyl,tri(C₁-C₄alkyl)silanyl, especially tri(methyl)silanyl, optionallysubstituted C₆-C₁₀aryl, especially phenyl, or optionally substitutedC₆-C₁₀perfluoroaryl, especially C₆F₅,

A¹¹ is hydrogen, halogen, especially F, or Cl; nitro, cyano, C₁-C₄alkyl,C₂-C₄alkenyl, C₁-C₄perfluoroalkyl, —O—C₁-C₄perfluoroalkyl,tri(C₁-C₄alkyl)silanyl, especially tri(methyl)silanyl, optionallysubstituted C₆-C₁₀aryl, especially phenyl, or optionally substitutedC₆-C₁₀perfluoroaryl, especially C₆F₅,

A¹² is hydrogen, halogen, especially F, or Cl; nitro, hydroxy, mercapto,amino, C₁-C₄alkyl, C₂-C₄alkenyl, C₁-C₄perfluoroalkyl, C₁-C₄alkoxy,—O—C₁-C₄perfluoroalkyl, —S—C₁-C₄alkyl, a group —(CH₂)_(r)X²⁰, wherein ris 1, or 2, X²⁰ is halogen, especially F, or Cl; hydroxy, cyano,—O—C₁-C₄alkyl, di(C₁-C₄alkyl)amino, —CO₂X²¹, wherein X²¹ is H, orC₁-C₄alkyl; —CH═CHCO₂X²², wherein X²² is C₁-C₄alkyl; —CH(O), —SO₂X²³,—SOX²³, —NC(O)X²³, —NSO₂X²³, —NHX²³, —N(X²³)₂, wherein X²³ isC₁-C₄alkyl; tri(C₁-C₄alkyl)siloxanyl, optionally substituted—O—C₆-C₁₀aryl, especially phenoxy, cyclohexyl, optionally substitutedC₆-C₁₀aryl, especially phenyl, or optionally substitutedC₆-C₁₀perfluoroaryl, especially C₆F₅,

A¹³ is hydrogen, nitro, cyano, C₁-C₄alkyl, C₂-C₄alkenyl,C₁-C₄perfluoroalkyl, —O—C₁-C₄perfluoroalkyl, tri(C₁-C₄alkyl)silanyl, oroptionally substituted C₆-C₁₀aryl, especially phenyl, and Z¹ and Z² areindependently of each other C₁-C₄perfluoroalkyl, or optionallysubstituted C₆-C₁₀aryl, especially hydrogen.

Examples of specific compounds are compounds B-1 to B-110 or B′-1 toB′-79 (see claim 7). Special emphasis among them is given to compoundsB′-1 to B′-79, especially B′-1, B′-2, B′-4 to B′-7, B′-10, B′-12, B′-17,B′-18, B′-24 to B′-26, B′-32, B′-34, B′-36, B′-39, B′-40, B′-42, B′-43,B′-45, B′-47 to B′-50, B′-53 to B′-55, B′-71, B′-72, B′-76, B′-78.Compounds of special industrial importance are the compounds of type B,corresponding to the above formula (Ic) wherein M¹ is Ir, of the numbers1-7, 9, 12, 17-18, 24, 32, 34, 36, 38-40, 42-43, 45, 47, 49-50, 53-54,71-74, 76-77, 80-83, and 85-110.

In a preferred embodiment of the present invention the metal complex offormula I is a compound of formula

wherein

M¹ is Co, or Fe, especially Ir, or Rh,

R¹, R², R³ and R⁴ are hydrogen, or halogen, especially F, or Cl;

R⁵ is optionally substituted C₆-C₁₀aryl, C₁-C₄alkyl,C₁-C₄perfluoroalkyl, C₁-C₄alkoxy, or —O—C₁-C₄perfluoroalkyl, especiallyphenyl,

R⁶ is hydrogen, halogen, especially F, or Cl; nitro, C₁-C₄alkyl,C₁-C₄perfluoroalkyl, C₁-C₄alkoxy, or optionally substituted C₆-C₁₀aryl,especially phenyl,

R⁷ is hydrogen, halogen, especially F, or Cl; C₁-C₄alkyl,C₁-C₄perfluoroalkyl, optionally substituted C₆-C₁₀aryl, especiallyphenyl, or optionally substituted C₆-C₁₀perfluoroaryl, especially C₆F₅,

R⁸ is hydrogen, C₁-C₄alkyl, C₁-C₈alkoxy, C₁-C₄perfluoroalkyl, optionallysubstituted C₆-C₁₀aryl, especially phenyl, or optionally substitutedC₆-C₁₀perfluoroaryl, especially C₆F₅,

R⁹ is hydrogen, halogen, especially F, or Cl; nitro, cyano, C₁-C₄alkyl,C₁-C₄perfluoroalkyl, C₁-C₄alkoxy, or optionally substituted C₆-C₁₀aryl,especially phenyl,

A¹⁰ is hydrogen, halogen, especially F, or Cl; nitro, cyano, C₁-C₄alkyl,C₂-C₄alkenyl, C₁-C₄perfluoroalkyl, —O—C₁-C₄perfluoroalkyl,tri(C₁-C₄alkyl)silanyl, especially tri(methyl)silanyl, optionallysubstituted C₆-C₁₀aryl, especially phenyl, or optionally substitutedC₆-C₁₀perfluoroaryl, especially C₆F₅,

A¹¹ is hydrogen, halogen, especially F, or Cl; nitro, cyano, C₁-C₄alkyl,C₂-C₄alkenyl, C₁-C₄perfluoroalkyl, —O—C₁-C₄perfluoroalkyl,tri(C₁-C₄alkyl)silanyl, especially tri(methyl)silanyl, optionallysubstituted C₆-C₁₀aryl, especially phenyl, or optionally substitutedC₆-C₁₀perfluoroaryl, especially C₆F₅,

A¹² is hydrogen, halogen, especially F, or Cl; nitro, hydroxy, mercapto,amino, C₁-C₄alkyl, C₂-C₄alkenyl, C₁-C₄perfluoroalkyl, C₁-C₄alkoxy,—O—C₁-C₄perfluoroalkyl, —S—C₁-C₄alkyl, a group —(CH₂)_(r)X²⁰, wherein ris 1, or 2, X²⁰ is halogen, especially F, or Cl; hydroxy, cyano,—O—C₁-C₄alkyl, di(C₁-C₄alkyl)amino, —CO₂X²¹, wherein X²¹ is H, orC₁-C₄alkyl; —CH═CHCO₂X²², wherein X²² is C₁-C₄alkyl; —CH(O), —SO₂X²³,—SOX²³, —NC(O)X²³, —NSO₂X²³, —NHX²³, —N(X²³)₂, wherein X²³ isC₁-C₄alkyl; tri(C₁-C₄alkyl)siloxanyl, optionally substituted—O—C₆-C₁₀aryl, especially phenoxy, cyclohexyl, optionally substitutedC₆-C₁₀aryl, especially phenyl, or optionally substitutedC₆-C₁₀perfluoroaryl, especially C₆F₅,

A¹³ is hydrogen, nitro, cyano, C₁-C₄alkyl, C₂-C₄alkenyl,C₁-C₄perfluoroalkyl, —O—C₁-C₄perfluoroalkyl, tri(C₁-C₄alkyl)silanyl, oroptionally substituted C₆-C₁₀aryl, especially phenyl, and Z¹, Z², Z³,Z⁴, Z⁵ and are independently of each other selected from the groupconsisting of hydrogen, C₁-C₂₄alkyl, C₁-C₂₄halogenalkyl,C₁-C₈perfluoroalkyl, C₂-C₂₄alkenyl, C₂-C₂₄alkynyl, C₂-C₂₄alkoxycarbonyl,aryl, which can optionally be substituted, C₁-C₂₄carboxylate,C₁-C₂₄alkoxy, C₂-C₂₄alkenyloxy, C₂-C₂₄alkynyloxy, or aryloxy, whereineach of Z¹, Z², Z³ and Z⁴ optionally being substituted with C₁-C₈alkyl,halogen, C₁-C₈alkoxy, or with a phenyl group, which can optionally besubstituted with halogen, C₁-C₈alkyl, or C₁-C₈alkoxy, or Z¹ and Z², ifpossible, form an aromatic or heteroaromatic ring, and/or Z³, Z⁴, Z⁵ andZ⁶, if possible, form an alkyl or heteroalkyl ring.

Examples of specific compounds are compounds C-1 to C-110 (see claim 7).Compounds of special industrial importance are those compounds C,corresponding to the above formula (Id) wherein M¹ is Ir, of the numbers1-7, 9, 12, 17-18, 24, 32, 34, 36, 38-40, 42-43, 45, 47, 49-50, 53-54,71-74, 76-77, 80-83, and 85-110.

In a preferred embodiment of the present invention the metal complex offormula I is a compound of formula

wherein M¹ is Co, or Fe, especially Ir, or Rh, R¹ is hydrogen, halogen,especially F, or Cl; nitro, cyano, C₁-C₄alkyl, C₁-C₄perfluoroalkyl, orC₁-C₄alkoxy,

R² is hydrogen, halogen, especially F, or Cl; nitro, cyano, C₁-C₄alkyl,C₁-C₄perfluoroalkyl, C₁-C₄alkoxy, —S—C₁-C₄alkyl, —O—C₁-C₄perfluoroalkyl,—SO₂X²², —CO₂X²², wherein X²² is C₁-C₄alkyl; C₆H₄CF₃, or optionallysubstituted —O—C₆-C₁₀aryl, especially phenoxy,

R³ is hydrogen, halogen, especially F, or Cl; nitro, cyano, C₁-C₄alkyl,C₁-C₄perfluoroalkyl, C₁-C₄alkoxy, —S—C₁-C₄alkyl, or—O—C₁-C₄perfluoroalkyl,

R⁴ is hydrogen, halogen, especially F, or Cl;

R⁵ is optionally substituted C₆-C₁₀aryl, C₁-C₄alkyl,C₁-C₄perfluoroalkyl, C₁-C₄alkoxy, or —O—C₁-C₄perfluoroalkyl, especiallyphenyl, and

Z¹ is C₁-C₄perfluoroalkyl, or optionally substituted C₆-C₁₀aryl,especially phenyl.

Examples of specific compounds are compounds D-1 to D-90 (see claim 7);special emphasis among them is given to compounds D-1 to D-30,especially D-2 to D-4, D-6, D-8, D-9, D-11, D-22 to D-28, D-30. Ofspecial industrial importance are those compounds D, corresponding tothe above formula (Ie) wherein M¹ is Ir, of the numbers 1-4, 6, 8-9, 11,22-24, 26-28, 31-34, 36, 38-39, 41, 52-54, 56-58, 61-64, 66, 68-69, 71,82-84, 86-88.

In a preferred embodiment of the present invention the metal complex offormula I is a compound of formula

wherein M¹ is Co, or Fe, especially Ir, or Rh, R¹ is hydrogen, halogen,especially F, or Cl; nitro, cyano, C₁-C₄alkyl, C₁-C₄perfluoroalkyl, orC₁-C₄alkoxy,

R² is hydrogen, halogen, especially F, or Cl; nitro, cyano, C₁-C₄alkyl,C₁-C₄perfluoroalkyl, C₁-C₄alkoxy, —S—C₁-C₄alkyl, —O—C₁-C₄perfluoroalkyl,—SO₂X²², —CO₂X²², wherein X²² is C₁-C₄alkyl; C₆H₄CF₃, or optionallysubstituted —O—C₈-C₁₀aryl, especially phenoxy,

R³ is hydrogen, halogen, especially F, or Cl; nitro, cyano, C₁-C₄alkyl,C₁-C₄perfluoroalkyl, C₁-C₄alkoxy, —S—C₁-C₄alkyl, or—O—C₁-C₄perfluoroalkyl,

R⁴ is hydrogen, halogen, especially F, or Cl;

R⁵ is optionally substituted C₈-C₁₀aryl, C₁-C₄alkyl,C₁-C₄perfluoroalkyl, C₁-C₄alkoxy, or —O—C₁-C₄perfluoroalkyl, especiallyphenyl, and

Z¹ is C₁-C₄perfluoroalkyl, or optionally substituted C₈-C₁₀aryl,especially phenyl.

Examples of specific compounds are compounds E-1 to E-90 (see claim 7);special emphasis among them is given to compounds E-1 to E-30,especially E-2 to E-4, E-6, E-8, E-9, E-11, E-22 to E-29. Of specialindustrial importance are those compounds E, corresponding to the aboveformula (If) wherein M¹ is Ir, of the numbers 1-4, 6, 8-9, 11, 22-24,26-28, 31-34, 36, 38-39, 41, 52-54, 56-58, 61-64, 66, 68-69, 71, 82-84,86-88.

In a preferred embodiment of the present invention the metal complex offormula I is a compound of formula

wherein M¹ is Co, or Fe, especially Ir, or Rh, R¹ is hydrogen, halogen,especially F, or Cl; nitro, cyano, C₁-C₄alkyl, C₁-C₄perfluoroalkyl, orC₁-C₄alkoxy,

R² is hydrogen, halogen, especially F, or Cl; nitro, cyano, C₁-C₄alkyl,C₁-C₄perfluoroalkyl, C₁-C₄alkoxy, —S—C₁-C₄alkyl, —O—C₁-C₄perfluoroalkyl,—SO₂X²², —CO₂X²², wherein X²² is C₁-C₄alkyl; C₆H₄CF₃, or optionallysubstituted —O—C₈-C₁₀aryl, especially phenoxy,

R³ is hydrogen, halogen, especially F, or Cl; nitro, cyano, C₁-C₄alkyl,C₁-C₄perfluoroalkyl, C₁-C₄alkoxy, —S—C₁-C₄alkyl, or—O—C₁-C₄perfluoroalkyl,

R⁴ is hydrogen, halogen, especially F, or Cl;

R⁵ is optionally substituted C₈-C₁₀aryl, C₁-C₄alkyl,C₁-C₄perfluoroalkyl, C₁-C₄alkoxy, or —O—C₁-C₄perfluoroalkyl, especiallyphenyl, and

Z¹ and Z² are independently of each other selected from the groupconsisting of hydrogen, C₁-C₂₄alkyl, C₁-C₂₄halogenalkyl,C₁-C₈perfluoroalkyl, C₂-C₂₄alkenyl, C₂-C₂₄alkynyl, C₂-C₂₄alkoxycarbonyl,aryl, aryl which can be substituted, C₁-C₂₄carboxylate, C₁-C₂₄alkoxy,C₂-C₂₄alkenyloxy, C₂-C₂₄alkynyloxy, or aryloxy, wherein each of Z¹ andZ² optionally being substituted with C₁-C₈alkyl, halogen, C₁-C₈alkoxy,or with a phenyl group, which can optionally be substituted withhalogen, C₁-C₈alkyl, or C₁-C₈alkoxy, or Z¹ and Z², if possible, form anaromatic or heteroaromatic ring. Z¹ is preferably C₁-C₄perfluoroalkyl,or optionally substituted C₆-C₁₀aryl, especially phenyl.

Examples of specific compounds are compounds F-1 to F-30 (see claim 7).Of special industrial importance are those compounds F, corresponding tothe above formula (Ig) wherein M¹ is Ir, of the numbers 1-4, 6, 8-9, 11,22-24, 26-28.

In a preferred embodiment of the present invention the metal complex offormula I is a compound of formula

wherein M¹ is Co, or Fe, especially Ir, or Rh, R¹ is hydrogen, halogen,especially F, or Cl; nitro, cyano, C₁-C₄alkyl, C₁-C₄perfluoroalkyl, orC₁-C₄alkoxy,

R² is hydrogen, halogen, especially F, or Cl; nitro, cyano, C₁-C₄alkyl,C₁-C₄perfluoroalkyl, C₁-C₄alkoxy, —S—C₁-C₄alkyl, —O—C₁-C₄perfluoroalkyl,—SO₂X²², —CO₂X²², wherein X²² is C₁-C₄alkyl; C₆H₄CF₃, or optionallysubstituted —O—C₆-C₁₀aryl, especially phenoxy,

R³ is hydrogen, halogen, especially F, or Cl; nitro, cyano, C₁-C₄alkyl,C₁-C₄perfluoroalkyl, C₁-C₄alkoxy, —S—C₁-C₄alkyl, or—O—C₁-C₄perfluoroalkyl,

R⁴ is hydrogen, halogen, especially F, or Cl;

R⁵ is optionally substituted C₆-C₁₀aryl, C₁-C₄alkyl,C₁-C₄perfluoroalkyl, C₁-C₄alkoxy, or —O—C₁-C₄perfluoroalkyl, especiallyphenyl, and

Z¹, Z², Z³, Z⁴, and Z⁵ are independently of each other selected from thegroup consisting of hydrogen, C₁-C₂₄alkyl, C₁-C₂₄halogenalkyl,C₁-C₈perfluoroalkyl, C₂-C₂₄alkenyl, C₂-C₂₄alkynyl, C₂-C₂₄alkoxycarbonyl,aryl, which can optionally be substituted, C₁-C₂₄carboxylate,C₁-C₂₄alkoxy, C₂-C₂₄alkenyloxy, C₂-C₂₄alkynyloxy, or aryloxy, whereineach of Z¹, Z², Z³ and Z⁴ optionally being substituted with C₁-C₈alkyl,halogen, C₁-C₈alkoxy, or with a phenyl group, which can optionally besubstituted with halogen, C₁-C₈alkyl, or C₁-C₈alkoxy, or Z¹ and Z², ifpossible, form an aromatic or heteroaromatic ring, and/or Z³, Z⁴, Z⁵ andZ⁶, if possible, form an alkyl or heteroalkyl ring. Z¹ is preferablyC₁-C₄perfluoroalkyl, or optionally substituted C₆-C₁₀aryl, especiallyphenyl.

Examples of specific compounds are compounds G-1 to G-30 (see claim 7).

In a preferred embodiment of the present invention the metal complex offormula I is a compound of formula

wherein

M¹ is Ni, Rh, or Ru, especially Pd, or Pt,

R¹, R², R³ and R⁴ are hydrogen, or halogen, especially F, or Cl;

R⁵ is optionally substituted C₆-C₁₀aryl, C₁-C₄alkyl,C₁-C₄perfluoroalkyl, C₁-C₄alkoxy, or —O—C₁-C₄perfluoroalkyl, especiallyphenyl,

R⁶ is hydrogen, halogen, especially F, or Cl; nitro, C₁-C₄alkyl,C₁-C₄perfluoroalkyl, C₁-C₄alkoxy, or optionally substituted C₆-C₁₀aryl,especially phenyl,

R⁷ is hydrogen, halogen, especially F, or Cl; C₁-C₄alkyl,C₁-C₄perfluoroalkyl, optionally substituted C₆-C₁₀aryl, especiallyphenyl, or optionally substituted C₆-C₁₀perfluoroaryl, especially C₆F₅,

R⁸ is hydrogen, C₁-C₄alkyl, C₁-C₈alkoxy, C₁-C₄perfluoroalkyl, optionallysubstituted C₆-C₁₀aryl, especially phenyl, or optionally substitutedC₆-C₁₀perfluoroaryl, especially C₆F₅,

R⁹ is hydrogen, halogen, especially F, or Cl; nitro, cyano, C₁-C₄alkyl,C₁-C₄perfluoroalkyl, C₁-C₄alkoxy, or optionally substituted C₆-C₁₀aryl,especially phenyl,

A¹⁰ is hydrogen, halogen, especially F, or Cl; nitro, cyano, C₁-C₄alkyl,C₂-C₄alkenyl, C₁-C₄perfluoroalkyl, —O—C₁-C₄perfluoroalkyl,tri(C₁-C₄alkyl)silanyl, especially tri(methyl)silanyl, optionallysubstituted C₆-C₁₀aryl, especially phenyl, or optionally substitutedC₆-C₁₀perfluoroaryl, especially C₆F₅,

A¹¹ is hydrogen, halogen, especially F, or Cl; nitro, cyano, C₁-C₄alkyl,C₂-C₄alkenyl, C₁-C₄perfluoroalkyl, —O—C₁-C₄perfluoroalkyl,tri(C₁-C₄alkyl)silanyl, especially tri(methyl)silanyl, optionallysubstituted C₆-C₁₀aryl, especially phenyl, or optionally substitutedC₆-C₁₀perfluoroaryl, especially C₆F₅,

A¹² is hydrogen, halogen, especially F, or Cl; nitro, hydroxy, mercapto,amino, C₁-C₄alkyl, C₂-C₄alkenyl, C₁-C₄perfluoroalkyl, C₁-C₄alkoxy,—O—C₁-C₄perfluoroalkyl, —S—C₁-C₄alkyl, a group —(CH₂)_(r)X²⁰, wherein ris 1, or 2, X²⁰ is halogen, especially F, or Cl; hydroxy, cyano,—O—C₁-C₄alkyl, di(C₁-C₄alkyl)amino, —CO₂X²¹, wherein X²¹ is H, orC₁-C₄alkyl; —CH═CHCO₂X²², wherein X²² is C₁-C₄alkyl; —CH(O), —SO₂X²³,—SOX²³, —NC(O)X²³, —NSO₂X²³, —NHX²³, —N(X²³)₂, wherein X²³ isC₁-C₄alkyl; tri(C₁-C₄alkyl)siloxanyl, optionally substituted—O—C₆-C₁₀aryl, especially phenoxy, cyclohexyl, optionally substitutedC₆-C₁₀aryl, especially phenyl, or optionally substitutedC₆-C₁₀perfluoroaryl, especially C₆F₅,

A¹³ is hydrogen, nitro, cyano, C₁-C₄alkyl, C₂-C₄alkenyl,C₁-C₄perfluoroalkyl, —O—C₁-C₄perfluoroalkyl, tri(C₁-C₄alkyl)silanyl, oroptionally substituted C₆-C₁₀aryl, especially phenyl, and Z¹ isC₁-C₄perfluoroalkyl, or optionally substituted C₆-C₁₀aryl, especiallyphenyl.

Examples of specific compounds are compounds H-1 to H-320 and H′-1 toH′-330 (see claim 7); special emphasis among them is given to compoundsH-1 to H-58, H-60 to H-79, H′-1 to H′-58, and H′-60 to H′-79; especiallyto H-1, H-2, H-4 to H-7, H-10, H-12, H-17, H-18, H-24 to H-26, H-32,H-34, H-36, H-39, H-40, H-42, H-43, H-45, H-47 to 50, H-53 to H-55,H-71, H-72, H-76, H-78, H′-1, H′-2, H′-4 to H′-7, H′-10, H′-12, H′-17,H′-18, H′-24 to H′-26, H′-32, H′-34, H′-36, H′-39, H′-40, H′-42, H′-43,H′-45, H′-47 to H′-50, H′-53 to H′-55, H′-71, H′-76, H′-78. Of specialindustrial importance are those compounds H, corresponding to the aboveformula (Ii) wherein M¹ is Pt, of the numbers 1-7, 9, 12, 17-18, 24, 32,34, 36, 38-40, 42-43, 45, 47, 49-50, 53-54, 71-74, 76-77, 80-83, 85-117,119, 127-128, 134, 142, 144, 146, 148-150, 152-153, 155, 157, 159-160,163-164, 181-184, 186-187, 190-193, 195-219, 222, 227-228, 234, 242,244, 246, 248-250, 252-253, 255, 257, 259-260, 263-264, 281-284,286-287, 290-293, 295-320; or those compounds H′, corresponding to theabove formula (Ij) wherein M¹ is Pt, of the numbers 1-7, 9, 12, 17-18,24, 32, 34, 36, 38-40, 42-43, 45, 47, 49-50, 53-54, 71-74, 76-77, 80-83,85-117, 119, 127-128, 134, 142, 144, 146, 148-150, 152-153, 155, 157,159-160, 163-164, 181-184, 186-187, 190-193, 195-227, 229, 232, 237-238,244, 252, 254, 256, 258-260, 262-263, 265, 267, 269-270, 273-274,291-294, 296-297, 300-303, 305-330.

In a preferred embodiment of the present invention the metal complex offormula I is a compound of formula

wherein

M¹ is Ni, Rh, or Ru, especially Pd, or Pt,

R¹, R², R³ and R⁴ are hydrogen, or halogen, especially F, or Cl;

R⁵ is optionally substituted C₆-C₁₀aryl, C₁-C₄alkyl,C₁-C₄perfluoroalkyl, C₁-C₄alkoxy, or —O—C₁-C₄perfluoroalkyl, especiallyphenyl,

R⁶ is hydrogen, halogen, especially F, or Cl; nitro, C₁-C₄alkyl,C₁-C₄perfluoroalkyl, C₁-C₄alkoxy, or optionally substituted C₆-C₁₀aryl,especially phenyl,

R⁷ is hydrogen, halogen, especially F, or Cl; C₁-C₄alkyl,C₁-C₄perfluoroalkyl, optionally substituted C₆-C₁₀aryl, especiallyphenyl, or optionally substituted C₆-C₁₀perfluoroaryl, especially C₆F₅,

R⁸ is hydrogen, C₁-C₄alkyl, C₁-C₈alkoxy, C₁-C₄perfluoroalkyl, optionallysubstituted C₆-C₁₀aryl, especially phenyl, or optionally substitutedC₆-C₁₀perfluoroaryl, especially C₆F₅,

R⁹ is hydrogen, halogen, especially F, or Cl; nitro, cyano, C₁-C₄alkyl,C₁-C₄perfluoroalkyl, C₁-C₄alkoxy, or optionally substituted C₆-C₁₀aryl,especially phenyl,

A¹⁰ is hydrogen, halogen, especially F, or Cl; nitro, cyano, C₁-C₄alkyl,C₂-C₄alkenyl, C₁-C₄perfluoroalkyl, —O—C₁-C₄perfluoroalkyl,tri(C₁-C₄alkyl)silanyl, especially tri(methyl)silanyl, optionallysubstituted C₆-C₁₀aryl, especially phenyl, or optionally substitutedC₆-C₁₀perfluoroaryl, especially C₆F₅,

A¹¹ is hydrogen, halogen, especially F, or Cl; nitro, cyano, C₁-C₄alkyl,C₂-C₄alkenyl, C₁-C₄perfluoroalkyl, —O—C₁-C₄perfluoroalkyl,tri(C₁-C₄alkyl)silanyl, especially tri(methyl)silanyl, optionallysubstituted C₆-C₁₀aryl, especially phenyl, or optionally substitutedC₆-C₁₀perfluoroaryl, especially C₆F₅,

A¹² is hydrogen, halogen, especially F, or Cl; nitro, hydroxy, mercapto,amino, C₁-C₄alkyl, C₂-C₄alkenyl, C₁-C₄perfluoroalkyl, C₁-C₄alkoxy,—O—C₁-C₄perfluoroalkyl, —S—C₁-C₄alkyl, a group —(CH₂)_(r)X²⁰, wherein ris 1, or 2, X²⁰ is halogen, especially F, or Cl; hydroxy, cyano,—O—C₁-C₄alkyl, di(C₁-C₄alkyl)amino, —CO₂X²¹, wherein X²¹ is H, orC₁-C₄alkyl; —CH═CHCO₂X²², wherein X²² is C₁-C₄alkyl; —CH(O), —SO₂X²³,—SOX²³, —NC(O)X²³, —NSO₂X²³, NHX²³, —N(X²³)₂, wherein X²³ is C₁-C₄alkyl;tri(C₁-C₄alkyl)siloxanyl, optionally substituted —O—C₆-C₁₀aryl,especially phenoxy, cyclohexyl, optionally substituted C₆-C₁₀aryl,especially phenyl, or optionally substituted C₆-C₁₀perfluoroaryl,especially C₆F₅,

A¹³ is hydrogen, nitro, cyano, C₁-C₄alkyl, C₂-C₄alkenyl,C₁-C₄perfluoroalkyl, —O—C₁-C₄perfluoroalkyl, tri(C₁-C₄alkyl)silanyl, oroptionally substituted C₆-C₁₀aryl, especially phenyl, and Z¹ and Z² areindependently of each other selected from the group consisting ofhydrogen, C₁-C₂₄alkyl, C₁-C₂₄halogenalkyl, C₁-C₈perfluoroalkyl,C₂-C₂₄alkenyl, C₂-C₂₄alkynyl, C₂-C₂₄alkoxycarbonyl, aryl, aryl which canbe substituted, C₁-C₂₄carboxylate, C₁-C₂₄alkoxy, C₂-C₂₄alkenyloxy,C₂-C₂₄alkynyloxy, or aryloxy. wherein each of Z¹ and Z² optionally beingsubstituted with C₁-C₈alkyl, halogen, C₁-C₈alkoxy, or with a phenylgroup, which can optionally be substituted with halogen, C₁-C₈alkyl, orC₁-C₈alkoxy, or Z¹ and Z², if possible, form an aromatic orheteroaromatic ring.

Examples of specific compounds are compounds I-1 to I-110 (see claim 7).Of special industrial importance are those compounds I, corresponding tothe above formula (Ik) wherein M¹ is Pt, of the numbers 1-7, 9, 12,17-18, 24, 32, 34, 36, 38-40, 42-43, 45, 47, 49-50, 53-54, 71-74, 76-77,80-83, 85-110.

In a preferred embodiment of the present invention the metal complex offormula I is a compound of formula

wherein

M¹ is Ni, Rh, or Ru, especially Pd, or Pt,

R¹, R², R³ and R⁴ are hydrogen, or halogen, especially F, or Cl;

R⁵ is optionally substituted C₆-C₁₀aryl, C₁-C₄alkyl,C₁-C₄perfluoroalkyl, C₁-C₄alkoxy, or —O—C₁-C₄perfluoroalkyl, especiallyphenyl,

R⁶ is hydrogen, halogen, especially F, or Cl; nitro, C₁-C₄alkyl,C₁-C₄perfluoroalkyl, C₁-C₄alkoxy, or optionally substituted C₆-C₁₀aryl,especially phenyl,

R⁷ is hydrogen, halogen, especially F, or Cl; C₁-C₄alkyl,C₁-C₄perfluoroalkyl, optionally substituted C₆-C₁₀aryl, especiallyphenyl, or optionally substituted C₆-C₁₀perfluoroaryl, especially C₆F₅,

R⁸ is hydrogen, C₁-C₄alkyl, C₁-C₈alkoxy, C₁-C₄perfluoroalkyl, optionallysubstituted C₆-C₁₀aryl, especially phenyl, or optionally substitutedC₆-C₁₀perfluoroaryl, especially C₆F₅,

R⁹ is hydrogen, halogen, especially F, or Cl; nitro, cyano, C₁-C₄alkyl,C₁-C₄perfluoroalkyl, C₁-C₄alkoxy, or optionally substituted C₆-C₁₀aryl,especially phenyl,

A¹⁰ is hydrogen, halogen, especially F, or Cl; nitro, cyano, C₁-C₄alkyl,C₂-C₄alkenyl, C₁-C₄perfluoroalkyl, —O—C₁-C₄perfluoroalkyl,tri(C₁-C₄alkyl)silanyl, especially tri(methyl)silanyl, optionallysubstituted C₆-C₁₀aryl, especially phenyl, or optionally substitutedC₆-C₁₀perfluoroaryl, especially C₆F₅,

A¹¹ is hydrogen, halogen, especially F, or Cl; nitro, cyano, C₁-C₄alkyl,C₂-C₄alkenyl, C₁-C₄perfluoroalkyl, —O—C₁-C₄perfluoroalkyl,tri(C₁-C₄alkyl)silanyl, especially tri(methyl)silanyl, optionallysubstituted C₆-C₁₀aryl, especially phenyl, or optionally substitutedC₆-C₁₀perfluoroaryl, especially C₆F₅,

A¹² is hydrogen, halogen, especially F, or Cl; nitro, hydroxy, mercapto,amino, C₁-C₄alkyl, C₂-C₄alkenyl, C₁-C₄perfluoroalkyl, C₁-C₄alkoxy,—O—C₁-C₄perfluoroalkyl, —S—C₁-C₄alkyl, a group —(CH₂)_(r)X²⁰, wherein ris 1, or 2, X²⁰ is halogen, especially F, or Cl; hydroxy, cyano,—O—C₁-C₄alkyl, di(C₁-C₄alkyl)amino, —CO₂X²¹, wherein X²¹ is H, orC₁-C₄alkyl; —CH═CHCO₂X²², wherein X²² is C₁-C₄alkyl; —CH(O), —SO₂X²³,—SOX²³, —NC(O)X²³, —NSO₂X²³, —NHX²³, —N(X²³)₂, wherein X²³ isC₁-C₄alkyl; tri(C₁-C₄alkyl)siloxanyl, optionally substituted—O—C₆-C₁₀aryl, especially phenoxy, cyclohexyl, optionally substitutedC₆-C₁₀aryl, especially phenyl, or optionally substitutedC₆-C₁₀perfluoroaryl, especially C₆F₅,

A¹³ is hydrogen, nitro, cyano, C₁-C₄alkyl, C₂-C₄alkenyl,C₁-C₄perfluoroalkyl, —O—C₁-C₄perfluoroalkyl, tri(C₁-C₄alkyl)silanyl, oroptionally substituted C₆-C₁₀aryl, especially phenyl, and Z¹, Z², Z³,and Z⁴ are independently of each other selected from the groupconsisting of hydrogen, C₁-C₂₄alkyl, C₁-C₂₄halogenalkyl,C₁-C₈perfluoroalkyl, C₂-C₂₄alkenyl, C₂-C₂₄alkynyl, C₂-C₂₄alkoxycarbonyl,aryl, aryl which can be substituted, C₁-C₂₄carboxylate, C₁-C₂₄alkoxy,C₂-C₂₄alkenyloxy, C₂-C₂₄alkynyloxy, or aryloxy, wherein each of Z¹, Z²,Z³ and Z⁴ optionally being substituted with C₁-C₈alkyl, halogen,C₁-C₈alkoxy, or with a phenyl group, which can optionally be substitutedwith halogen, C₁-C₈alkyl, or C₁-C₈alkoxy, or Z¹ and Z², if possible,form an aromatic or heteroaromatic ring, and/or Z³ and Z⁴, if possible,form an alkyl or heteroalkyl ring.

Examples of specific compounds are compounds J-1 to J-110 (see claim 7).Of special industrial importance are those compounds J, corresponding tothe above formula (II) wherein M¹ is Pt, of the numbers 1-7, 9, 12,17-18, 24, 32, 34, 36, 38-40, 42-43, 45, 47, 49-50, 53-54, 71-74, 76-77,80-83, 85-110.

In a preferred embodiment of the present invention the metal complex offormula I is a compound of formula

wherein

M¹ Ni, Rh, or Ru, especially Pd, or Pt,

R¹ is hydrogen, halogen, especially F, or Cl; nitro, cyano, C₁-C₄alkyl,C₁-C₄perfluoroalkyl, or C₁-C₄alkoxy,

R² is hydrogen, halogen, especially F, or Cl; nitro, cyano, C₁-C₄alkyl,C₁-C₄perfluoroalkyl, C₁-C₄alkoxy, —S—C₁-C₄alkyl, —O—C₁-C₄perfluoroalkyl,—SO₂X²², —CO₂X²², wherein X²² is C₁-C₄alkyl; C₆H₄CF₃, or optionallysubstituted —O—C₆-C₁₀aryl, especially phenoxy,

R³ is hydrogen, halogen, especially F, or Cl; nitro, cyano, C₁-C₄alkyl,C₁-C₄perfluoroalkyl, C₁-C₄alkoxy, —S—C₁-C₄alkyl, or—O—C₁-C₄perfluoroalkyl,

R⁴ is hydrogen, halogen, especially F, or Cl;

R⁵ is optionally substituted C₆-C₁₀aryl, C₁-C₄alkyl,C₁-C₄perfluoroalkyl, C₁-C₄alkoxy, or —O—C₁-C₄perfluoroalkyl, especiallyphenyl, and

Z¹ is C₁-C₄perfluoroalkyl, or optionally substituted C₆-C₁₀aryl,especially phenyl.

Examples of specific compounds are compounds K-1 to K-90 and K′-1 toK′-90 (see claim 7); special emphasis among them is given to compoundsK-1 to K-30 and K′-1 to K′-30; especially to K-2 to K-4, K-6, K-8, K-9,K-11, K-15, K-22 to K-28, K′-2 to K′-4, K′-6, K′-8, K′-9, K′-11, K′-15,K′-22 to K′-28. Of special industrial importance are those compounds Kand K′, corresponding to the above formulae (Im) and (In) wherein M¹ isPt, of the numbers 1-6, 8-9, 11, 23-25, 27-29, 31-36, 38-39, 41, 52-54,56-58, 61-66, 68-69, 71, 82-84, 86-88.

In a preferred embodiment of the present invention the metal complex offormula I is a compound of formula

wherein

M¹ is Ni, Rh, or Ru, especially Pd, or Pt,

R¹ is hydrogen, halogen, especially F, or Cl; nitro, cyano, C₁-C₄alkyl,C₁-C₄perfluoroalkyl, or C₁-C₄alkoxy,

R² is hydrogen, halogen, especially F, or Cl; nitro, cyano, C₁-C₄alkyl,C₁-C₄perfluoroalkyl, C₁-C₄alkoxy, —S—C₁-C₄alkyl, —O—C₁-C₄perfluoroalkyl,—SO₂X²², —CO₂X²², wherein X²² is C₁-C₄alkyl; C₆H₄CF₃, or optionallysubstituted —O—C₆-C₁₀aryl, especially phenoxy,

R³ is hydrogen, halogen, especially F, or Cl; nitro, cyano, C₁-C₄alkyl,C₁-C₄perfluoroalkyl, C₁-C₄alkoxy, —S—C₁-C₄alkyl, or—O—C₁-C₄perfluoroalkyl,

R⁴ is hydrogen, halogen, especially F, or Cl;

R⁵ is optionally substituted C₆-C₁₀aryl, C₁-C₄alkyl,C₁-C₄perfluoroalkyl, C₁-C₄alkoxy, or —O—C₁-C₄perfluoroalkyl, especiallyphenyl, and

Z¹ and Z² are independently of each other selected from the groupconsisting of hydrogen, C₁-C₂₄alkyl, C₁-C₂₄halogenalkyl,C₁-C₈perfluoroalkyl, C₂-C₂₄alkenyl, C₂-C₂₄alkynyl, C₂-C₂₄alkoxycarbonyl,aryl, aryl which can be substituted, C₁-C₂₄carboxylate, C₁-C₂₄alkoxy,C₂-C₂₄alkenyloxy, C₂-C₂₄alkynyloxy, or aryloxy, wherein each of Z¹ andZ² optionally being substituted with C₁-C₈alkyl, halogen, C₁-C₈alkoxy,or with a phenyl group, which can optionally be substituted withhalogen, C₁-C₈alkyl, or C₁-C₈alkoxy, or Z¹ and Z², if possible, form anaromatic or heteroaromatic ring. Z¹ is preferably C₁-C₄perfluoroalkyl,or optionally substituted C₆-C₁₀aryl, especially phenyl.

Examples of specific compounds are compounds L-1 to L-30 (see claim 7).Of special industrial importance are those compounds L corresponding tothe above formula (Io) wherein M¹ is Pt, of the numbers 1-6, 8-9, 11,22-24, 26-28.

In a preferred embodiment of the present invention the metal complex offormula I is a compound of formula

wherein

M¹ is Ni, Rh, or Ru, especially Pd, or Pt,

R¹ is hydrogen, halogen, especially F, or Cl; nitro, cyano, C₁-C₄alkyl,C₁-C₄perfluoroalkyl, or C₁-C₄alkoxy,

R² is hydrogen, halogen, especially F, or Cl; nitro, cyano, C₁-C₄alkyl,C₁-C₄perfluoroalkyl, C₁-C₄alkoxy, —S—C₁-C₄alkyl, —O—C₁-C₄perfluoroalkyl,—SO₂X²², —CO₂X²², wherein X²² is C₁-C₄alkyl; C₆H₄CF₃, or optionallysubstituted —O—C₆-C₁₀aryl, especially phenoxy,

R³ is hydrogen, halogen, especially F, or Cl; nitro, cyano, C₁-C₄alkyl,C₁-C₄perfluoroalkyl, C₁-C₄alkoxy, —S—C₁-C₄alkyl, or—O—C₁-C₄perfluoroalkyl,

R⁴ is hydrogen, halogen, especially F, or Cl;

R⁵ is optionally substituted C₆-C₁₀aryl, C₁-C₄alkyl,C₁-C₄perfluoroalkyl, C₁-C₄alkoxy, or —O—C₁-C₄perfluoroalkyl, especiallyphenyl, and

Z¹, Z², Z³ and Z⁴ are independently of each other selected from thegroup consisting of hydrogen, C₁-C₂₄alkyl, C₁-C₂₄halogenalkyl,C₁-C₈perfluoroalkyl, C₂-C₂₄alkenyl, C₂-C₂₄alkynyl, C₂-C₂₄alkoxycarbonyl,aryl, which can optionally be substituted, C₁-C₂₄carboxylate,C₁-C₂₄alkoxy, C₂-C₂₄alkenyloxy, C₂-C₂₄alkynyloxy, or aryloxy, whereineach of Z¹, Z², Z³ and Z⁴ optionally being substituted with C₁-C₈alkyl,halogen, C₁-C₈alkoxy, or with a phenyl group, which can optionally besubstituted with halogen, C₁-C₈alkyl, or C₁-C₈alkoxy, or Z¹ and Z², ifpossible, form an aromatic or heteroaromatic ring, and/or Z³, Z⁴, Z⁵ andZ⁶, if possible, form an alkyl or heteroalkyl ring. Z¹ is preferablyC₁-C₄perfluoroalkyl, or optionally substituted C₆-C₁₀aryl, especiallyphenyl.

Examples of specific compounds are compounds M-1 to M-30 (see claim 7).Of special industrial importance are those compounds L corresponding tothe above formula (Ip) wherein M¹ is Pt, of the numbers 1-6, 8-9, 11,22-24, 26-28.

Examples of further specific compounds are given below:

Halogen is fluorine, chlorine, bromine and iodine.

C₁-C₂₄alkyl, especially C₁-C₈alkyl, is a branched or unbranched radicalsuch as for example methyl, ethyl, propyl, isopropyl, n-butyl,sec-butyl, isobutyl, tert-butyl, 2-ethylbutyl, n-pentyl, isopentyl,1-methylpentyl, 1,3-dimethylbutyl, n-hexyl, 1-methylhexyl, n-heptyl,isoheptyl, 1,1,3,3-tetra methyl butyl, 1-methyl heptyl, 3-methyl heptyl,n-octyl, 2-ethyl hexyl, 1,1,3-trimethylhexyl, 1,1,3,3-tetramethylpentyl,nonyl, decyl, undecyl, 1-methylundecyl, dodecyl,1,1,3,3,5,5-hexamethylhexyl, tridecyl, tetradecyl, pentadecyl,hexadecyl, heptadecyl, octadecyl, icosyl or docosyl.

C₁-C₂₄perfluoroalkyl, especially C₁-C₄perfluoroalkyl, is a branched orunbranched radical such as for example —CF₃, —CF₂CF₃, —CF₂CF₂CF₃,—CF(CF₃)₂, —(CF₂)₃CF₃, and —C(CF₃)₃.

C₁-C₂₄alkoxy radicals are straight-chain or branched alkoxy radicals,e.g. methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy,tert-butoxy, amyloxy, isoamyloxy or tert-amyloxy, heptyloxy, octyloxy,isooctyloxy, nonyloxy, decyloxy, undecyloxy, dodecyloxy, tetradecyloxy,pentadecyloxy, hexadecyloxy, heptadecyloxy and octadecyloxy.

C₂-C₂₄alkenyl radicals are straight-chain or branched alkenyl radicals,such as e.g. vinyl, allyl, methallyl, isopropenyl, 2-butenyl, 3-butenyl,isobutenyl, n-penta-2,4-dienyl, 3-methyl-but-2-enyl, n-oct-2-enyl,n-dodec-2-enyl, isododecenyl, n-dodec-2-enyl or n-octadec-4-enyl.

C₂₋₂₄alkynyl is straight-chain or branched and preferably C₂₋₈alkynyl,which may be unsubstituted or substituted, such as, for example,ethynyl, 1-propyn-3-yl, 1-butyn-4-yl, 1-pentyn-5-yl,2-methyl-3-butyn-2-yl, 1,4-pentadiyn-3-yl, 1,3-pentadiyn-5-yl,1-hexyn-6-yl, cis-3-methyl-2-penten-4-yn-1-yl,trans-3-methyl-2-penten-4-yn-1-yl, 1,3-hexadiyn-5-yl, 1-octyn-8-yl,1-nonyn-9-yl, 1-decyn-10-yl, or 1-tetracosyn-24-yl.

C₄-C₁₈cycloalkyl, especially C₆-C₁₂cycloalkyl, is preferablyC₆-C₁₂cycloalkyl or said cycloalkyl substituted by one to threeC₁-C₄alkyl groups, such as, for example, cyclopentyl,methyl-cyclopentyl, dimethylcyclopentyl, cyclohexyl, methylcyclohexyl,di methylcyclohexyl, trimethyl-cyclohexyl, tert-butylcyclohexyl,cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, cyclododecyl,1-adamantyl, or 2-adamantyl. Cyclohexyl, 1-adamantyl and cyclopentyl aremost preferred.

Examples of C₄-C₁₈cycloalkyl, which is interrupted by S, O, or NR⁵, arepiperidyl, piperazinyl and morpholinyl.

Aryl is usually C₆-C₃₀aryl, preferably C₆-C₂₄aryl, which optionally canbe substituted, such as, for example, phenyl, 4-methylphenyl,4-methoxyphenyl, naphthyl, biphenylyl, 2-fluorenyl, phenanthryl,anthryl, tetracyl, pentacyl, hexacyl, terphenylyl or quadphenylyl; orphenyl substituted by one to three C₁-C₄alkyl groups, for example o-, m-or p-methylphenyl, 2,3-dimethylphenyl, 2,4-dimethylphenyl,2,5-dimethylphenyl, 2,6-dimethylphenyl, 3,4-dimethylphenyl,3,5-dimethylphenyl, 2-methyl-6-ethylphenyl, 4-tert-butylphenyl,2-ethylphenyl or 2,6-diethylphenyl. Important examples for C₆-C₁₀arylare phenyl and naphthyl, especially phenyl.

C₇-C₂₄aralkyl radicals are preferably C₇-C₁₅aralkyl radicals, which maybe substituted, such as, for example, benzyl, 2-benzyl-2-propyl,β-phenethyl, α-methyl benzyl, α,α-dimethylbenzyl, ω-phenyl-butyl,ω-phenyl-octyl, ω-phenyl-dodecyl; or phenyl-C₁-C₄alkyl substituted onthe phenyl ring by one to three C₁-C₄alkyl groups, such as, for example,2-methylbenzyl, 3-methylbenzyl, 4-methyl benzyl, 2,4-dimethylbenzyl,2,6-dimethylbenzyl or 4-tert-butylbenzyl.or3-methyl-5-(1′,1′,3′,3′-tetramethyl-butyl)-benzyl.

Heteroaryl is typically C₂-C₂₆heteroaryl, i.e. a ring with five to sevenring atoms or a condensed rig system, wherein nitrogen, oxygen or sulfurare the possible hetero atoms, and is typically an unsaturatedheterocyclic radical with five to 30 atoms having at least sixconjugated π-electrons such as thienyl, benzo[b]thienyl,dibenzo[b,d]thienyl, thianthrenyl, furyl, furfuryl, 2H-pyranyl,benzofuranyl, isobenzofuranyl, dibenzofuranyl, phenoxythienyl, pyrrolyl,imidazolyl, pyrazolyl, pyridyl, bipyridyl, triazinyl, pyrimidinyl,pyrazinyl, pyridazinyl, indolizinyl, isoindolyl, indolyl, indazolyl,purinyl, quinolizinyl, chinolyl, isochinolyl, phthalazinyl,naphthyridinyl, chinoxalinyl, chinazolinyl, cinnolinyl, pteridinyl,carbazolyl, carbolinyl, benzotriazolyl, benzoxazolyl, phenanthridinyl,acridinyl, perimidinyl, phenanthrolinyl, phenazinyl, isothiazolyl,phenothiazinyl, isoxazolyl, furazanyl or phenoxazinyl, which can beunsubstituted or substituted.

C₆-C₁₈cycloalkoxy is, for example, cyclopentyloxy, cyclohexyloxy,cycloheptyloxy or cyclooctyloxy, or said cycloalkoxy substituted by oneto three C₁-C₄alkyl, for example, methylcyclopentyloxy,dimethylcyclopentyloxy, methylcyclohexyloxy, dimethylcyclohexyloxy,trimethylcyclohexyloxy, or tert-butylcyclohexyloxy.

C₆-C₂₄aryloxy is typically phenoxy or phenoxy substituted by one tothree C₁-C₄alkyl groups, such as, for example o-, m- or p-methylphenoxy,2,3-dimethylphenoxy, 2,4-dimethylphenoxy, 2,5-dimethylphenoxy,2,6-dimethylphenoxy, 3,4-dimethylphenoxy, 3,5-dimethylphenoxy,2-methyl-6-ethylphenoxy, 4-tert-butylphenoxy, 2-ethylphenoxy or2,6-diethylphenoxy.

C₆-C₂₄aralkoxy is typically phenyl-C₁-C₉alkoxy, such as, for example,benzyloxy, α-methylbenzyloxy, α,α-dimethylbenzyloxy or 2-phenylethoxy.

C₁-C₂₄alkylthio radicals are straight-chain or branched alkylthioradicals, such as e.g. methylthio, ethylthio, propylthio, isopropylthio,n-butylthio, isobutylthio, pentylthio, isopentyl-thio, hexylthio,heptylthio, octylthio, decylthio, tetradecylthio, hexadecylthio oroctadecylthio.

Examples of a ring formed by Z³, Z⁴, Z⁵ and Z⁶, respectively arecycloalkanes having from 3 to 7 carbon atoms or heterocycloalkaneshaving from 3 to 6 carbon atoms which can have one or more additionalhetero atoms selected from nitrogen, oxygen and sulfur, for example,cyclopentane, cyclohexane, pyrrolidine, pyrimidine, or morpholine, whichcan optionally be substituted by one or more C₁-C₈alkyl groups.

Examples of a ring formed by Z¹ and Z² are aryl groups having from 6 to10 carbon atoms which can have one or more additional hetero atomsselected from nitrogen, oxygen and sulfur, and which can optionally besubstituted by, for example, one or more C₁-C₈alkyl groups, such asbenzene.

An example, wherein ring A and ring B form an additional ring is

Possible substituents of the above-mentioned groups are C₁-C₈alkyl, ahydroxyl group, a mercapto group, C₁-C₈alkoxy, C₁-C₈alkylthio, halogen,halo-C₁-C₈alkyl, a cyano group, an aldehyde group, a ketone group, acarboxyl group, an ester group, a carbamoyl group, an amino group, anitro group or a silyl group.

The term “haloalkyl” means groups given by partially or whollysubstituting the above-mentioned alkyl group with halogen, such astrifluoromethyl etc. The “aldehyde group, ketone group, ester group,carbamoyl group and amino group” include those substituted by anC₁-C₂₄alkyl group, a C₄-C₁₈cycloalkyl group, an C₆-C₃₀aryl group, anC₇-C₂₄aralkyl group or a heterocyclic group, wherein the alkyl group,the cycloalkyl group, the aryl group, the aralkyl group and theheterocyclic group may be unsubstituted or substituted. The term “silylgroup” means a group of formula —SiR¹⁰⁵R¹⁰⁶R¹⁰⁷, wherein R¹⁰⁵, R¹⁰⁶ andR¹⁰⁷ are independently of each other a C₁-C₈alkyl group, in particular aC₁-C₄alkyl group, a C₆-C₂₄aryl group or a C₇-C₁₂aralkylgroup, such as atrimethylsilyl group.

If a substituent occurs more than one time in a group, it can bedifferent in each occurrence.

The synthesis of the tetrakis-(C^N)-μ-(dichloro)-diiridium(III)complexes can, for example, be done according to the procedure describedin M. Nonoyama, Bull. Chem. Soc. Jp. 1974, 47, 767, or M. E. Thompson etal., J. Am. Chem. Soc., 2001, 123, 4304. The (C^N) ligand (L²) isstirred in the presence of iridium(III) chloride in a mixture ofethanol/water at 120° C. for 8 to 24 hours. After filtration a productis obtained which is used in the next step of the synthesis withoutfurther purification.

In case the carbene is created from5-methoxy-1,3,4-triphenyl-1,2,4(5H)-triazoline, it is obtained byheating of 5-methoxy-1,3,4-triphenyl-1,2,4(5H)-triazoline at 80° C. for8 to 24 hours. The iridium dimer of formula X is added to a solution ofthe carbene in toluene, whereby the iridium complex of formula XI isobtained. The iridium complex of formula XI can be purified bychromatography, or precipitation, for example, in hexane.

5-methoxy-1,3,4-triphenyl-1,2,4(5H)-triazoline is commercially availableor can be prepared according to the procedure described in gemäss D.Ender et al., Synthesis 2003, 8, 1292.

The synthesis of the tris-cyclometalated Ir(III) complexes can be doneaccording to the procedure by M. E. Thompson et al., J. Am. Chem. Soc.,2003, 125, 7377, by heating thetetrakis-(C^N)-μ-(dichloro)-diiridium(III) complexes in the presence ofappropriate cyclometalating ligand and a base, like potassium carbonatein glycerol or by the reaction of cyclometalating ligand in the presenceif Ir(acac)₃ at elevated temperature as described by S. Kwon et al. inEur. J. Inorg. Chem. 2004, 3415 or by R. J. Wattse et al. in Inorg Chem.1991, 30, 1687. Alternatively the tris-cyclometalated Ir(III) complexescan be prepared as described by M. C. DeRosa et al. in J. Am. Chem.Soc., 2004, 126, 7619, by the reaction of thetetrakis-(C^N)-μ-(dichloro)-diiridium(III) with silver triflate andsubsequent treatment with the appropriate cyclometalating ligand.

Dichloride-bridged dimers of the general structure C^NPt(μ-Cl)₂PtC^N canbe done according to the procedure described by M. E. Thompson et al. inInorg. Chem., 2002, 41 (12), 3055 by the reaction of potassiumtetrachloroplatinate with a cyclometalating ligand precursor (HC^N) in2-ethoxyethanol.K₂PtCl₄+HC^N →C^NPt(μ-Cl)₂PtC^N

The dimers can be dissociated in the presence of a base and appropriatecyclometalating ligands as described by M. E. Thompson et al., Inorg.Chem., 2002, 41 (12), 3055.

The present invention is also directed to an electronic devicecomprising the metal complex and its fabrication process. The electronicdevice can comprise at least one organic active material positionedbetween two electrical contact layers, wherein at least one of thelayers of the device includes the metallic complex compound. Theelectronic device can comprise an anode layer (a), a cathode layer (e),and an active layer (c). Adjacent to the anode layer (a) is an optionalhole-injecting/transport layer (b), and adjacent to the cathode layer(e) is an optional electron-injection/transport layer (d). Layers (b)and (d) are examples of charge transport layers.

The active layer (c) can comprise at least approximately 1 weightpercent of metal complex previously described.

In some embodiments, the active layer (c) may be substantially 100% ofthe metal complex because a host charge transporting material, such asAlq₃ is not needed. By “substantially 100%” it is meant that the metalcomplex is the only material in the layer, with the possible exceptionof impurities or adventitious by-products from the process to form thelayer. Still, in some embodiments, the metal complex may be a dopantwithin a host material, which is typically used to aid charge transportwithin the active layer (c). The active layer (c), including any of themetal complexes, can be a small molecule active material.

The device may include a support or substrate (not shown) adjacent tothe anode layer (a) or the cathode layer (e). Most frequently, thesupport is adjacent the anode layer (a). The support can be flexible orrigid, organic or inorganic. Generally, glass or flexible organic filmsare used as a support. The anode layer (a) is an electrode that is moreefficient for injecting holes compared to the cathode layer (e). Theanode can include materials containing a metal, mixed metal, alloy,metal oxide or mixed-metal oxide. Suitable metal elements within theanode layer (a) can include the Groups 4, 5, 6, and 8-11 transitionmetals. If the anode layer (a) is to be light transmitting, mixed-metaloxides of Groups 12, 13 and 14 metals, such as indium-tin-oxide, may beused. Some non-limiting, specific examples of materials for anode layer(a) include indium-tin-oxide (“ITO”), aluminum-tin-oxide, gold, silver,copper, nickel, and selenium.

The anode layer (a) may be formed by a chemical or physical vapordeposition process or spin-cast process. Chemical vapor deposition maybe performed as a plasma-enhanced chemical vapor deposition (“PECVD”) ormetal organic chemical vapor deposition (“MOCVD”).

Physical vapor deposition can include all forms of sputtering (e. g.,ion beam sputtering), e-beam evaporation, and resistance evaporation.

Specific forms of physical vapor deposition include rf magnetronsputtering or inductively-coupled plasma physical vapordeposition(“ICP-PVD”). These deposition techniques are well-known withinthe semiconductor fabrication arts.

A hole-transport layer (b) may be adjacent the anode. Both holetransporting small molecule compounds and polymers can be used.

Commonly used hole transporting molecules include: polyvinyl-carbazol,N,N′-diphenyl-N, N′-bis(3-methylphenyl)-[1,1′-biphenyl]-4,4′-diamine(TPD), 1,1-bis[(di-4-tolylamino)phenyl]cyclohexane (TAPC),N,N′-bis(4-methylphenyl)-N,N′-bis(4-ethylphenyl)-[1,1′-(3,3′-dimethyl)biphenyl]4,4′-diamine(ETPD), tetrakis-(3-methylphenyl)-N,N,N′,N′-2,5-phenylenediamine (PDA),a-phenyl-4-N,N-diphenylaminostyrene (TPS),p-(diethylamino)benzaldehydediphenyl hydrazone (DEH), triphenylamine(TPA), bis[4-(N,N-diethylamino)-2-methylphenyl](4-methylphenyl)methane(MPMP),1-phenyl-3-[p-(diethylamino)styryl]-5-[p-(diethylamino)phenyl]pyrazoline(PPR or DEASP), 1,2-trans-bis (9H-carbazol-9-yl)cyclobutane (DCZB),N,N,N′,N′-tetrakis (4-methylphenyl)-(1,1′-biphenyl)-4,4′-diamine (TTB),4,4′-N,N-dicarbazole-biphenyl (CBP),N,N-dicarbazoyl-1,4-dimethene-benzene (DCB), porphyrinic compounds, andcombinations thereof.

Commonly used hole transporting polymers are polyvinylcarbazole,(phenylmethyl) polysilane, poly(3,4-ethylendioxythiophene) (PEDOT), andpolyaniline. Hole-transporting polymers can be obtained by dopinghole-transporting molecules such as those mentioned above into polymerssuch as polystyrene and polycarbonate.

The hole-injection/transport layer (b) can be formed using anyconventional means, including spin-coating, casting, and printing, suchas gravure printing. The layer can also be applied by ink jet printing,thermal patterning, or chemical, or physical vapor deposition.

Usually, the anode layer (a) and the hole-injection/transport layer (b)are patterned during the same lithographic operation. The pattern mayvary as desired. The layers can be formed in a pattern by, for example,positioning a patterned mask or resist on the first flexible compositebarrier structure prior to applying the first electrical contact layermaterial. Alternatively, the layers can be applied as an overall layer(also called blanket deposit) and subsequently patterned using, forexample, a patterned resist layer and wet-chemical or dry-etchingtechniques. Other processes for patterning that are well known in theart can also be used. When the electronic devices are located within anarray, the anode layer (a) and hole injection/transport layer (b)typically are formed into substantially parallel strips having lengthsthat extend in substantially the same direction.

The active layer (c) may comprise the metal complexes described herein.The particular material chosen may depend on the specific application,potentials used during operation, or other factors. The active layer (c)may comprise a host material capable of transporting electrons and/orholes, doped with an emissive material that may trap electrons, holes,and/or excitons, such that excitons relax from the emissive material viaa photoemissive mechanism. Active layer (c) may comprise a singlematerial that combines transport and emissive properties. Whether theemissive material is a dopant or a major constituent, the active layermay comprise other materials, such as dopants that tune the emission ofthe emissive material. Active layer (c) may include a plurality ofemissive materials capable of, in combination, emitting a desiredspectrum of light. Examples of phosphorescent emissive materials includethe metal complexes of the present invention. Examples of fluorescentemissive materials include DCM and DMQA. Examples of host materialsinclude Alq₃, CBP and mCP. Examples of emissive and host materials aredisclosed in U.S. Pat. No. 6,303,238, which is incorporated by referencein its entirety.

The active layer (c) can be applied from solutions by any conventionaltechnique, including spin coating, casting, and printing. The activeorganic materials can be applied directly by vapor deposition processes,depending upon the nature of the materials.

Optional layer (d) can function both to facilitate electroninjection/transport, and also serve as a buffer layer or confinementlayer to prevent quenching reactions at layer interfaces. Morespecifically, layer (d) may promote electron mobility and reduce thelikelihood of a quenching reaction if layers (c) and (e) would otherwisebe in direct contact. Examples of materials for optional layer (d)include metal-cheated oxinoid compounds (e. g.,tris(8-hydroxyquinolato)aluminum (Alq₃) or the like);phenanthroline-based compounds (e. g.,2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (“DDPA”),4,7-diphenyl-1,10-phenanthroline (“DPA”), or the like; azole compounds(e. g., 2-(4-biphenyl)-5-(4-t-butylphenyl)-1,3,4-oxadiazole (“PBD”) orthe like, 3-(4-biphenyl)-4-phenyl-5-(4-t-butylphenyl)-1,2,4-triazole(“TAZ”) or the like; other similar compounds; or any one or morecombinations thereof. Alternatively, optional layer (d) may be inorganicand comprise BaO, LiF, Li₂O, or the like.

The electron injection/transport layer (d) can be formed using anyconventional means, including spin-coating, casting, and printing, suchas gravure printing. The layer can also be applied by ink jet printing,thermal patterning, or chemical or physical vapor deposition.

The cathode layer (e) is an electrode that is particularly efficient forinjecting electrons or negative charge carriers. The cathode layer (e)can be any metal or nonmetal having a lower work function than the firstelectrical contact layer (in this case, the anode layer (a)). Materialsfor the second electrical contact layer can be selected from alkalimetals of Group 1 (e. g., Li, Na, K, Rb, Cs), the Group 2 (alkalineearth) metals, the Group 12 metals, the rare earths, the lanthanides (e.g., Ce, Sm, Eu, or the like), and the actinides. Materials, such asaluminum, indium, calcium, barium, yttrium, and magnesium, andcombinations thereof, may also be used. Li-containing organometalliccompounds, LiF, and Li₂O can also be deposited between the organic layerand the cathode layer to lower the operating voltage. Specificnon-limiting examples of materials for the cathode layer (e) includebarium, lithium, cerium, cesium, europium, rubidium, yttrium, magnesium,or samarium.

The cathode layer (e) is usually formed by a chemical or physical vapordeposition process. In general, the cathode layer will be patterned, asdiscussed above in reference to the anode layer (a) and optional holeinjecting layer (b). If the device lies within an array, the cathodelayer (e) may be patterned into substantially parallel strips, where thelengths of the cathode layer strips extend in substantially the samedirection and substantially perpendicular to the lengths of the anodelayer strips.

Electronic elements called pixels are formed at the cross points (wherean anode layer strip intersects a cathode layer strip when the array isseen from a plan or top view).

In other embodiments, additional layer (s) may be present within organicelectronic devices. For example, a layer (not shown) between the holeinjecting layer (b) and the active layer (c) may facilitate positivecharge transport, band-gap matching of the layers, function as aprotective layer, or the like. Similarly, additional layers (not shown)between the electron injecting layer (d) and the cathode layer (e) mayfacilitate negative charge transport, band-gap matching between thelayers, function as a protective layer, or the like. Layers that areknown in the art can be used. Some or all of the layers may be surfacetreated to increase charge carrier transport efficiency. The choice ofmaterials for each of the component layers may be determined bybalancing the goals of providing a device with high device efficiencywith the cost of manufacturing, manufacturing complexities, orpotentially other factors.

The charge transport layers (b) and (d) are generally of the same typeas the active layer (c). More specifically, if the active layer (c) hasa small molecule compound, then the charge transport layers (b) and (d),if either or both are present, can have a different small moleculecompound. If the active layer (c) has a polymer, the charge transportlayers (b) and (d), if either or both are present, can also have adifferent polymer. Still, the active layer (c) may be a small moleculecompound, and any of its adjacent charge transport layers may bepolymers.

Each functional layer may be made up of more than one layer. Forexample, the cathode layer may comprise a layer of a Group I metal and alayer of aluminum. The Group I metal may lie closer to the active layer(c), and the aluminum may help to protect the Group I metal fromenvironmental contaminants, such as water.

Although not meant to limit, the different layers may have the followingrange of thicknesses: inorganic anode layer (a), usually no greater thanapproximately 500 nm, for example, approximately 50-200 nm; optionalhole-injecting layer (b), usually no greater than approximately 100 nm,for example, approximately 50-200 nm; active layer (c), usually nogreater than approximately 100 nm, for example, approximately 10-80 nm;optional electron-injecting layer (d), usually no greater thanapproximately 100 nm, for example, approximately 10-80 nm; and cathodelayer (e), usually no greater than approximately 1000 nm, for example,approximately 30-500 nm. If the anode layer (a) or the cathode layer (e)needs to transmit at least some light, the thickness of such layer maynot exceed approximately 100 nm.

The location of the electron-hole recombination zone in the device, andthus the emission spectrum of the device, can be affected by therelative thickness of each layer. For example, when a potentiallight-emitting compound, such as Alq₃ is used in the electron transportlayer (d), the electron-hole recombination zone can lie within the Alq₃layer.

The emission would then be that of Alq₃, and not a desired sharpemission. Thus, the thickness of the electron-transport layer should bechosen so that the electron-hole recombination zone lies within thelight-emitting layer (i. e., active layer (c)). The desired ratio oflayer thicknesses can depend on the exact nature of the materials used.

The efficiency of the devices made with metal complexes can be furtherimproved by optimizing the other layers in the device. For example, moreefficient cathodes such as Ca, Ba, Mg/Ag, or LiF/Al can be used. Shapedsubstrates and hole transport materials that result in a reduction inoperating voltage or increase quantum efficiency are also applicable.Additional layers can also be added to tailor the energy levels of thevarious layers and facilitate electroluminescence.

Depending upon the application of the electronic device, the activelayer (c) can be a light-emitting layer that is activated by a signal(such as in a light-emitting diode) or a layer of material that respondsto radiant energy and generates a signal with or without an appliedpotential (such as detectors or voltaic cells). Examples of electronicdevices that may respond to radiant energy are selected fromphotoconductive cells, photoresistors, photoswitches, phototransistors,and phototubes, and photovoltaic cells. After reading thisspecification, skilled artisans will be capable of selecting material(s) that for their particular applications.

The electroluminescent devices may be employed for full color displaypanels in, for example, mobile phones, televisions and personal computerscreens. Accordingly the present invention relates also to a deviceselected from stationary and mobile displays, such as displays forcomputers, mobile phones, laptops, pdas, TV sets, displays in printers,kitchen equipment, billboards, lightings, information boards anddestination boards in trains and buses, containing an organic lightemitting diode according to the present invention.

In OLEDs, electrons and holes, injected from the cathode (e) and anode(a) layers, respectively, into the photoactive layer (c), form negativeand positively charged polarons in the active layer (c). These polaronsmigrate under the influence of the applied electric field, forming apolaron exciton with an oppositely charged species and subsequentlyundergoing radiative recombination. A sufficient potential differencebetween the anode and cathode, usually less than approximately 20 volts,and in some instances no greater than approximately 5 volts, may beapplied to the device. The actual potential difference may depend on theuse of the device in a larger electronic component. In many embodiments,the anode layer (a) is biased to a positive voltage and the cathodelayer (e) is at substantially ground potential or zero volts during theoperation of the electronic device. A battery or other power source (s)may be electrically connected to the electronic device as part of acircuit.

In other embodiments, the metal complex compound can be used as a chargetransport material in layer (b) or (d).

The compound does not need to be in a solid matrix diluent (e. g., hostcharge transport material) when used in layer (b) (c), or (d) in orderto be effective. A layer greater than approximately 1% by weight of themetal complex compound, based on the total weight of the layer, and upto substantially 100% of the complex compound can be used as the activelayer (c). Additional materials can be present in the active layer (c)with the complex compound. For example, a fluorescent dye may be presentto alter the color of emission.

A diluent may also be added. The diluent can be a polymeric material,such as poly (N-vinyl carbazole) and polysilane. It can also be a smallmolecule, such as 4,4′-N,N′-dicarbazole biphenyl or tertiary aromaticamines. When a diluent is used, the complex compound is generallypresent in a small amount, usually less than 20% by weight, preferablyless than 10% by weight, based on the total weight of the layer.

The metallic complexes may be used in applications other than electronicdevices. For example, the complexes may be used as catalysts orindicators (e. g., oxygen-sensitive indicators, phosphorescentindicators in bioassays, or the like).

The following examples illustrate certain features and advantages of thepresent invention. They are intended to be illustrative of theinvention, but not limiting. All percentages are by weight, unlessotherwise indicated. Abbreviations, used in claims or elsewhere, areknown in the art and include the following ones:

Ph phenyl

t- denotes a tertiary (alkyl) group, such as t-Bu standing for tertiarybutyl

Bu butyl

LC liquid chromatography

MS mass spectrometry

CIE International Commission on Illumination

EXAMPLES Example 1

a) Tetrakis(2-phenylpyridinato-C²,N′)(μ-dichloro)-diiridium(III)

In a 100 ml 3-necked-flask equipped with a reflux condenseriridum(III)chloride hydrate (201.2 mg, 0.67 mmol, 1 eq.) is partiallysolved in 25 ml of a 3:1 mixture of 2-ethoxyethanol and water (degassedwith N₂) giving an olive-green solution and a brown-black insolublesolid. 2-Phenylpyridine (0.4 ml, 2.80 mmol, 4.2 eq.) is then added andthe reaction mixture heated to 120° C.; the insoluble solid dissolvesand an orange-yellow precipitate appears. After stirring over night at120° C. and cooling at room temperature the yellow product is filteredoff, washed with ethanol and acetone and dried in vacuo giving a yellowpowder. Yield: 265.5 mg (0.25 mmol, 73%), yellow powder.

b) Synthesis of 1,2,4-Triazol-2-ium-5-ylidene Iridium (III) complex

In a dried Schlenck tube 85.5 mg (0.26 mmol, 2.4 eq.) ofmethoxy-1,3,4-triphenyl-1,2,4(5H)-triazoline are heated to 90° C. undervacuum over night. After cooling, 9 ml of toluene are added to the freecarbene, followed by 115.6 mg (0.11 mmol, 1 eq.) oftetrakis(2-phenylpyridinato-C²,N′)(μ-dichloro)-diiridium(III). Theyellow suspension is stirred for 4 h at 120° C. After cooling thereaction mixture is diluted with toluene and extracted with 10% NaHCO₃(5×15 ml). The organic phase is dried over NaSO₄, the solvent isevaporated and the crude product is purified by column chromatography(dichloromethane, 7.5 g silica) giving a yellow solid (yield: 77.4 mg(47%)).

MS (+TOF MS): m/z 797.2157 ([M]⁺), 643.1429 ([M-ppy]⁺), 501.0947([M-PhTri]⁺); λ_(PL, sol) (toluene): 499 nm.

Example 2

According to the procedure described in Example 1 0.06 g (26% yield) ofthe compound below are obtained after chromatography.

MS (LC-MS, ES+): m/z 909.5 ([M]⁺); 699.5 ([M-C₁₃H₈NS]⁺); λ_(PL, sol)(toluene): 547 nm.

Example 3

According to the procedure described in Example 1 1.10 g (55% yield) ofthe compound below are obtained after precipitation.

MS (LC-MS, ES+): m/z 909.3 ([M]⁺); λ_(PL, sol) (toluene): 590 nm.

Example 4

According to the procedure described in Example 1 0.1 g (70% yield) ofthe compound below are obtained after chromatography.

MS (LC-MS, ES+): m/z 869.7 ([M]⁺); λ_(PL, sol) (toluene): 485 nm.

Example 5

According to the procedure described in Example 1 0.073 g (24% yield) ofthe compound below are obtained after chromatography.

MS (LC-MS, ES+): m/z 929.6 ([M]⁺); λ_(PL, sol) (toluene): 471 nm.

Example 6

According to the procedure described in Example 1 0.50 g (45% yield) ofthe compound below are obtained after chromatography.

MS (LC-MS, ES+): m/z 897.4 ([M]⁺); λ_(PL, sol) (toluene): 608 nm.

Example 7

According to the procedure described in Example 1 0.50 g (45% yield) ofthe compound below are obtained after chromatography.

MS (LC-MS, ES+): m/z 897.4 ([M]⁺); λ_(PL, sol) (toluene): 612 nm.

Example 8

According to the procedure described in Example 1 0.16 g (58% yield) ofthe compound below are obtained after chromatography.

MS (APCI MS): m/z 998 ([M+1⁺), λ_(PL, sol) (toluene): 648 nm

Example 9

According to the procedure described in Example 1 0.16 g (58% yield) ofthe compound below are obtained after chromatography.

MS (+TOF MS): m/z 968.1 ([M]⁺); 729.1 ([M-C₁₂H₆F₄N]⁺), λ_(PL, sol)(toluene): 511 nm.

Example 10

According to the procedure described in Example 1 0.09 g (41% yield) ofthe compound below are obtained after chromatography.

MS (LC-MS, ES+): m/z 775 ([M]⁺); 632 ([M-ppz]⁺); λ_(PL, sol) (toluene):469 nm/500 nm.

Example 11

According to the procedure described in Example 1 0.09 g (31% yield) ofthe compound below are obtained after chromatography.

MS (EI-MS): m/z 877 ([M]⁺); λ_(PL, sol) (toluene): 570 nm.

Example 12

a) In a dried Schlenk tube under nitrogen 9 ml of a 3:1 mixture of1-propanol and water is added and degassed. 2-phenylpyridine (250 μl,1.75 mmol, 2.5 eq.) and potassium tetrachloroplatinate(II) (0.29 g, 0.70mmol, 1 eq.) is then added and the reaction mixture is heated to 120° C.After stirring over night at this temperature and cooling to roomtemperature the yellow product is filtered off and washed with ethanol.The product is purified by column chromatography (heptan:ethylacetate:3:1) giving a yellow solid. Yield: 0.24 g (89%), yellow powder.

b) According to the procedure described in Example 1 0.16 g (47% yield)of the compound below are obtained.

MS (+TOF MS): m/z 646 ([M]⁺); λ_(PL, sol) (toluene): 484 nm/516 nm.

Example 13

1-Methyl-3-phenyl-imidazolium trifluoromethanesulfonic acid (0.09 g,0.32 mmol) were placed in a dried Schlenk tube under nitrogen andstirred at room temperature for 45 minutes in 3.3 ml of THF. The yellowsuspension was cooled down to −60° C. and lithiumdiisopropylamid (0.35mmol, THF solution) was added. The reactions mixture was warmed up toroom temperature, and then solvent was removed by evaporation. Theresidue was dissolved in 5.1m1 toluene andtetrakis[2-(2-pyridinyl-N)phenyl-C]-di- -chlorodi-iridium(III) (0.20 g,0.19 mmol) and triethylamine (43.8 μl, 0.32 mmol) were added. Thereaction mixture was stirred for 18 hours at 100° C. After cooling, thereaction mixture was diluted with dichloromethane and extracted twicewith water. The organic phase was dried over NaSO₄, the solventevaporated and the crude product purified by column chromatography.After crystallization from dichloromrthane/hexane 0.05 g (22%) ofproduct were obtained.

MS (+TOF MS): m/z 659 ([M]⁺)

Example 14

In a Schlenk tube1,4-diphenyl-3-(trifluoromethyl)-4H-1,2,4-triazol-1-ium (0.47 g, 1.19mmol), potassium tert.-butylate (0.13 g, 1.19 mmol) and o-xylene (16 ml)are stirred at 90° C. for 4 hours. Thentetrakis[3,5-difluoro-2-(4-methoxy-2-pyridinyl-N)phenyl-C]di--chlorodi-iridium(III) (0.2 g, 0.15 mmol) is added and the reactionmixture is stirred at 135° C. for 20 hours. After cooling the solvent isremoved by evaporation. The crude product is purified by columnchromatography and crystallized from dichloromethane/hexane giving 0.08g (29%) of the product.

MS (+TOF MS): m/z 920 ([M]⁺); λ_(PL, sol) (toluene): 484 nm.

Example 15

The crude product is prepared according to the procedure described inExample 1, purified by column chromatography and crystallized fromdichloromethane/hexane giving 0.09 g (27%) of the product.

MS (+TOF MS): m/z 854 ([M]⁺); λ_(PL, sol) (toluene): 500 nm.

Application Examples

Device structure: On a glass substrate the following layer aresuperimposed: ITO (anode, 150 nm), PEDOT:PSS (100 nm), then the electroluminescent-polymer consisting of PVK, PBD, TPD, and 5% of thecorresponding emitter (80 nm), finally barium (5 nm) and aluminum(cathode, 100 nm).

Emission Ex. Quantum maximum Efficiency CIE Efficiency Compound (nm)(cd/A) Coordinates [%] A-1 527 4.4 0.30/0.57 1.2 A-80 487 0.31 0.26/0.330.16 A-82 610 3.2 0.65/0.34 3.1 A-81 487 0.28 0.31/0.36 0.15 A-164 4870.28 0.31/0.36 0.15

The invention claimed is:
 1. A compound of formula (I)

wherein the ring A,

 represents an optionally substituted aryl group which can optionallycontain heteroatoms, the ring B,

 represents an optionally substituted nitrogen containing aryl group,which can optionally contain further heteroatoms, or the ring A may betaken with the ring B binding to the ring A to form a ring; the group C,

 represents an acyclic carbene or a cyclic carbene (ring C), which canoptionally contain heteroatoms, the ring D,

 represents an optionally substituted aryl group which can optionallycontain heteroatoms, n1 is an integer of 1 to 3, m1 is an integer of 0,1 or 2, m2 is an integer 0 or 1, M¹ is a metal with an atomic weight ofgreater than 40, L³ is a monodentate ligand or a bidentate ligand, Y is—C(═O)— or —C(X¹)₂—, wherein X¹ is hydrogen or C₁₋₄alkyl and y is 0 or1; with the proviso that the following compounds

wherein L-L=η⁴−1,5-cyclooctadiene and Ar=2,6-diisopropylphenyl, areexcluded.
 2. The compound of claim 1, wherein the metal M¹ is selectedfrom the group consisting of Tl, Pb, Bi, In, Sn, Sb, Te, Mo, Cr, Mn, Ta,V, Cu, Fe, Ru, Ni, Co, Ir, Pt, Pd, Rh, Re, Os, Ag and Au.
 3. Thecompound of claim 2, wherein the metal M¹ is selected from the groupconsisting of Pt, Pd, Ag, Au, Ru and Ir.
 4. The compound of claim 1,wherein

is a group of formula

wherein R¹ to R⁴ are substitutents and can be taken together to form aring, y is 0 or 1, the group C,

 is a nucleophilic carbene of formula

wherein R⁵ is hydrogen, C₁-C₂₄alkyl, C₂-C₂₄alkenyl, C₂-C₂₄alkynyl,C₂-C₂₄alkoxycarbonyl, C₁-C₂₄carboxylate, C₁-C₂₄alkoxy, C₂-C₂₄alkenyloxy,C₂-C₂₄alkynyloxy or aryloxy, which can optionally be substituted withC₁-C₈alkyl, halogen, C₁-C₈alkoxy or with a phenyl group which can besubstituted with halogen, C₁-C₈alkyl, C₁-C₈alkoxy or aryl, which canoptionally be substituted; and R⁶, Z¹, Z², Z³, Z⁴, Z⁵ and Z⁶ areindependently of each other selected from the group consisting ofhydrogen, C₁-C₂₄alkyl, C₁-C₂₄halogenalkyl, C₂-C₂₄alkenyl, C₂-C₂₄alkynyl,C₂-C₂₄alkoxycarbonyl, aryl, C₁-C₂₄carboxylate, C₁-C₂₄alkoxy,C₂-C₂₄alkenyloxy, C₂-C₂₄alkynyloxy and aryloxy, with each of Z¹, Z², Z³and Z⁴ optionally being substituted with C₁-C₈alkyl, halogen,C₁-C₈alkoxy or with a phenyl group, which can optionally be substitutedwith halogen, C₁-C₈alkyl or C₁-C₈alkoxy, or Z¹ and Z² form an aromaticor heteroaromatic ring, and/or Z³, Z⁴, Z⁵ and Z⁶ form an alkyl orheteroalkyl ring.
 5. The compound of claim 4, wherein R¹, R², R³ and R⁴are independently of each other hydrogen, halogen, nitro, cyano,C₁-C₄alkyl, C₁-C₄perfluoroalkyl, C₁-C₄alkoxy, —S—C₁-C₄alkyl,—O—C₁-C₄perfluoroalkyl, —SO₂X²², —CO₂H, —CO₂X²², wherein X²² isC₁-C₄alkyl; C₆H₄CF₃, cyclohexyl, optionally substituted C₆-C₁₀aryl,optionally substituted —O—CH₂-C₆-C₁₀aryl or optionally substituted—O—C₆-C₁₀aryl.
 6. The compound of claim 5, wherein R¹, R², R³ and R⁴ areindependently of each other hydrogen, F, Cl, nitro, cyano, C₁-C₄alkyl,C₁-C₄perfluoroalkyl, C₁-C₄alkoxy, —S—C₁-C₄alkyl, —O—C₁-C₄perfluoroalkyl,—SO₂X²², —CO₂H, —CO₂X²², wherein X²² is C₁-C₄alkyl; C₆H₄CF₃, cyclohexyl,optionally substituted phenyl, optionally substituted benzyloxy oroptionally substituted phenoxy.
 7. The compound of claim 1, wherein

is a group of formula

wherein R⁶, R⁷, R⁸ and R⁹ are independently of each other hydrogen,C₁-C₂₄alkyl, C₂-C₂₄alkenyl, C₂-C₂₄alkynyl, aryl, heteroaryl,C₁-C₂₄alkoxy, C₁-C₂₄alkylthio, cyano, C₂-C₂₄acyl,C₁-C₂₄alkyloxycarbonyl, a nitro group or a halogen atom; and the ring Arepresents an optionally substituted aryl or heteroaryl group; or thering A may be taken with the pyridyl group binding to the ring A to forma ring; where the alkyl group, alkenyl group, alkynyl group, aryl group,heteroaryl group, alkoxy group, alkylthio group, acyl group andalkyloxycarbonyl group represented by R⁶, R⁷, R⁸ and R⁹ may besubstituted.
 8. The compound of claim 1, wherein L³ is a bidentateligand selected from the group consisting of

wherein R¹¹ and R¹⁵ are independently of each other hydrogen,C₁-C₈alkyl, C₆-C₁₈aryl, C₂-C₁₀heteroaryl or C₁-C₈perfluoroalkyl, R¹² andR¹⁶ are independently of each other hydrogen or C₁-C₈alkyl, R¹³ and R¹⁷are independently of each other hydrogen, C₁-C₈alkyl, C₆-C₁₈aryl,C₂-C₁₀heteroaryl, C₁-C₈perfluoroalkyl or C₁-C₈alkoxy, R¹⁴ is C₁-C₈alkyl,C₆-C₁₀aryl, C₇-C₁₁aralkyl or C₁-C₈alkoxy, R¹⁸ is C₆-C₁₀aryl, R¹⁹ isC₁-C₈alkyl, R²⁰ is C₁-C₈alkyl or C₆-C₁₀aryl, R²¹ is hydrogen, C₁-C₈alkylor C₁-C₈alkoxy, which may be partially or fully fluorinated, R²² and R²³are independently of each other C_(n)(H+F)_(2n+1) or C₆(H+F)₅, R²⁴ canbe the same or different at each occurrence and is selected from H andC_(n)(H+F)_(2n+1), p is 2 or 3 and R⁴⁶ is C₁-C₈alkyl, C₆-C₁₈aryl,C₁-C₈alkoxy or C₆-C₁₈aryl, which is substituted by C₁-C₈alkyl.
 9. Thecompound of claim 1 selected from the group consisting of

Cpd. R⁵ R⁶ R⁷ R⁸ R⁹ A¹⁰ A¹¹ A¹² A¹³ Z¹ A-1 Ph H H H H H H H H Ph A-2 PhH H H H H H CH₃ H Ph A-3 Ph H H H H H H Ph H Ph A-4 Ph H H H H H H t-BuH Ph A-5 Ph H H H H H H C₆H₁₁ H Ph A-6 Ph H H H H H H F H Ph A-7 Ph H HH H H H OCH₃ H Ph A-8 Ph H H H H H H OC₆H₅ H Ph A-9 Ph H H H H H H OH HPh A-10 Ph H H H H H H OCF₃ H Ph A-11 Ph H H H H H H OSi(CH₃)₂C(CH₃)₃ HPh A-12 Ph H H H H H H CF₃ H Ph A-13 Ph H H H H H H SCH₃ H Ph A-14 Ph HH H H H H SO₂CH₃ H Ph A-15 Ph H H H H H H SOCH₃ H Ph A-16 Ph H H H H H HSH H Ph A-17 Ph H H H H H H NO₂ H Ph A-18 Ph H H H H H H N(CH₃)₂ H PhA-19 Ph H H H H H H NH₂ H Ph A-20 Ph H H H H H H NCOCH₃ H Ph A-21 Ph H HH H H H NSO₂CH₃ H Ph A-22 Ph H H H H H H HNCH₂CH₃ H Ph A-23 Ph H H H H HH CHO H Ph A-24 Ph H H H H H H CH₂OH H Ph A-25 Ph H H H H H H CH₂Br H PhA-26 Ph H H H H H H CH₂CN H Ph A-27 Ph H H H H H H CH₂CO₂H H Ph A-28 PhH H H H H H CH₂OCH₃ H Ph A-29 Ph H H H H H H CH₂N(CH₂CH₃)₂ H Ph A-30 PhH H H H H H CHCHCO₂CH₃ H Ph A-31 Ph H H H H H H CH₂CH₂CO₂CH₃ H Ph A-32Ph H H H H H H C₆F₅ H Ph A-33 Ph H H H H H H H CH₃ Ph A-34 Ph H H H H HCH₃ H H Ph A-35 Ph H H H H H H H CHCH₂ Ph A-36 Ph H H H H H CHCH₂ H H PhA-37 Ph H H H H H H H Ph Ph A-38 Ph H H H H H Ph H H Ph A-39 Ph H H H HH C₆F₅ H H Ph A-40 Ph H H H H H CF₃ H CF₃ Ph A-41 Ph H H H H H H H CF₃Ph A-42 Ph H H H H H CF₃ H H Ph A-43 Ph H H H H H F H H Ph A-44 Ph H H HH H H H F Ph A-45 Ph H H H H H F H F Ph A-46 Ph H H H H H H H OCF₃ PhA-47 Ph H H H H H OCF₃ H H Ph A-48 Ph H H H H H NO₂ H CF₃ Ph A-49 Ph H HH H H CF₃ H NO₂ Ph A-50 Ph H H H H H CN H H Ph A-51 Ph H H H H H H H CNPh A-52 Ph H H H H H H H Si(CH₃)₃ Ph A-53 Ph H H H H H Si(CH₃)₃ H H PhA-54 Ph H H H H H NO₂ H CN Ph A-55 Ph H H H H H CN H NO₂ Ph A-56 Ph CF₃H H H H H H H Ph A-57 Ph Cl H H H H H H H Ph A-58 Ph NO₂ H H H H H H HPh A-59 Ph CN H H H H H H H Ph A-60 Ph CH₃ H H H H H H H Ph A-61 Ph OCH₃H H H H H H H Ph A-62 Ph Ph H H H H H H H Ph A-63 Ph F H H H H H H H PhA-64 Ph H H H CF₃ H H H H Ph A-65 Ph H H H CN H H H H Ph A-66 Ph H H HNO₂ H H H H Ph A-67 Ph H H H CH₃ H H H H Ph A-68 Ph H H H Ph H H H H PhA-69 Ph H H H F H H H H Ph A-70 Ph H H H OCH₃ H H H H Ph A-71 Ph H H CF₃H H H H H Ph A-72 Ph H H CH₃ H H H H H Ph A-73 Ph H CF₃ H H H H H H PhA-74 Ph H CH₃ H H H H H H Ph A-75 Ph H F H H H H H H Ph A-76 Ph H C₆F₅ HH H H H H Ph A-77 Ph H H C₆F₅ H H H H H Ph A-78 Ph H C₆H₅ H H H H H H PhA-79 Ph H H C₆H₅ H H H H H Ph A-80 Ph H H OCH₃ H F H F H Ph A-81 Ph HCF₃ H H H H F H Ph A-82 Ph H H ¹⁾ ¹⁾ H H H H Ph A-83 Ph H H H H HSi(CH₃)₂C₆F₁₃ H H Ph A-84 Ph H H OCH₃ H H F F H CF₃ A-85 Ph H C₆F₅ H H HH F H Ph A-86 Ph H C₆F₅ H H H H CF₃ H Ph A-87 Ph H C₆F₅ H H H C₆F₅ H HPh A-88 Ph H C₆F₅ H H H H C₆F₅ H Ph A-89 Ph H H C₆F₅ H H C₆F₅ H H PhA-90 Ph H H C₆F₅ H H H C₆F₅ H Ph A-91 Ph H H OCH₃ H F H F H Ph A-92 Ph HH OCH₃ H F CN F H Ph A-93 Ph H H OCH₃ H CF₃ H CF₃ H Ph A-94 Ph H HN(CH₃)₂ H F H F H PH A-95 Ph H H N(CH₃)₂ H F CN F H Ph A-96 Ph H HN(CH₃)₂ H CF₃ H CF₃ H Ph A-97 Ph ¹⁾ ¹⁾ H H H H H H Ph A-98 Ph ¹⁾ ¹⁾ H HH H CH₃ H Ph A-99 Ph ¹⁾ ¹⁾ H H H H OCH₃ H Ph A-100 Ph ¹⁾ ¹⁾ H H H HN(CH₃)₂ H Ph A-101 Ph ¹⁾ ¹⁾ H H H CH₃ H H Ph A-102 Ph ¹⁾ ¹⁾ H H H OCH₃ HH Ph A-103 Ph ¹⁾ ¹⁾ H H H N(CH₃)₂ H H Ph A-104 Ph H H ¹⁾ ¹⁾ H H H H PhA-105 Ph H H ¹⁾ ¹⁾ H H CH₃ H Ph A-106 Ph H H ¹⁾ ¹⁾ H H OCH₃ H Ph A-107Ph H H ¹⁾ ¹⁾ H H N(CH₃)₂ H Ph A-108 Ph H H ¹⁾ ¹⁾ H CH₃ H H Ph A-109 Ph HH ¹⁾ ¹⁾ H OCH₃ H H Ph A-110 Ph H H ¹⁾ ¹⁾ H N(CH₃)₂ H H Ph A-111 Ph H H HH H H H H CF₃ A-112 Ph H H H H H H CH₃ H CF₃ A-113 Ph H H H H H H Ph HCF₃ A-114 Ph H H H H H H t-Bu H CF₃ A-115 Ph H H H H H H C₆H₁₁ H CF₃A-116 Ph H H H H H H F H CF₃ A-117 Ph H H H H H H OCH₃ H CF₃ A-118 Ph HH H H H H OC₆H₅ H CF₃ A-119 Ph H H H H H H OH H CF₃ A-120 Ph H H H H H HOCF₃ H CF₃ A-121 Ph H H H H H H OSi(CH₃)₂C(CH₃)₃ H CF₃ A-122 Ph H H H HH H CF₃ H CF₃ A-123 Ph H H H H H H SCH₃ H CF₃ A-124 Ph H H H H H HSO₂CH₃ H CF₃ A-125 Ph H H H H H H SOCH₃ H CF₃ A-126 Ph H H H H H H SH HCF₃ A-127 Ph H H H H H H NO₂ H CF₃ A-128 Ph H H H H H H N(CH₃)₂ H CF₃A-129 Ph H H H H H H NH₂ H CF₃ A-130 Ph H H H H H H NCOCH₃ H CF₃ A-131Ph H H H H H H NSO₂CH₃ H CF₃ A-132 Ph H H H H H H HNCH₂CH₃ H CF₃ A-133Ph H H H H H H CHO H CF₃ A-134 Ph H H H H H H CH₂OH H CF₃ A-135 Ph H H HH H H CH₂Br H CF₃ A-136 Ph H H H H H H CH₂CN H CF₃ A-137 Ph H H H H H HCH₂CO₂H H CF₃ A-138 Ph H H H H H H CH₂OCH₃ H CF₃ A-139 Ph H H H H H HCH₂N(CH₂CH₃)₂ H CF₃ A-140 Ph H H H H H H CHCHCO₂CH₃ H CF₃ A-141 Ph H H HH H H CH₂CH₂CO₂CH₃ H CF₃ A-142 Ph H H H H H H C₆F₅ H CF₃ A-143 Ph H H HH H H H CH₃ CF₃ A-144 Ph H H H H H CH₃ H H CF₃ A-145 Ph H H H H H H HCHCH₂ CF₃ A-146 Ph H H H H H CHCH₂ H H CF₃ A-147 Ph H H H H H H H Ph CF₃A-148 Ph H H H H H Ph H H CF₃ A-149 Ph H H H H H C₆F₅ H H CF₃ A-150 Ph HH H H H CF₃ H CF₃ CF₃ A-151 Ph H H H H H H H CF₃ CF₃ A-152 Ph H H H H HCF₃ H H CF₃ A-153 Ph H H H H H F H H CF₃ A-154 Ph H H H H H H H F CF₃A-155 Ph H H H H H F H F CF₃ A-156 Ph H H H H H H H OCF₃ CF₃ A-157 Ph HH H H H OCF₃ H H CF₃ A-158 Ph H H H H H NO₂ H CF₃ CF₃ A-159 Ph H H H H HCF₃ H NO₂ CF₃ A-160 Ph H H H H H CN H H CF₃ A-161 Ph H H H H H H H CNCF₃ A-152 Ph H H H H H H H Si(CH₃)₃ CF₃ A-163 Ph H H H H H Si(CH₃)₃ H HCF₃ A-164 Ph H H H H H NO₂ H CN CF₃ A-165 Ph H H H H H CN H NO₂ CF₃A-166 Ph CF₃ H H H H H H H CF₃ A-167 Ph Cl H H H H H H H CF₃ A-168 PhNO₂ H H H H H H H CF₃ A-169 Ph CN H H H H H H H CF₃ A-170 Ph CH₃ H H H HH H H CF₃ A-171 Ph OCH₃ H H H H H H H CF₃ A-172 Ph Ph H H H H H H H CF₃A-173 Ph F H H H H H H H CF₃ A-174 Ph H H H CF₃ H H H H CF₃ A-175 Ph H HH CN H H H H CF₃ A-176 Ph H H H NO₂ H H H H CF₃ A-177 Ph H H H CH₃ H H HH CF₃ A-178 Ph H H H Ph H H H H CF₃ A-179 Ph H H H F H H H H CF₃ A-180Ph H H H OCH₃ H H H H CF₃ A-181 Ph H H CF₃ H H H H H CF₃ A-182 Ph H HCH₃ H H H H H CF₃ A-183 Ph H CF₃ H H H H H H CF₃ A-184 Ph H CH₃ H H H HH H CF₃ A-185 Ph H F H H H H H H CF₃ A-186 Ph H C₆F₅ H H H H H H CF₃A-187 Ph H H C₆F₅ H H H H H CF₃ A-188 Ph H C₆H₅ H H H H H H CF₃ A-189 PhH H C₆H₅ H H H H H CF₃ A-190 Ph H CF₃ H H H H F H CF₃ A-191 Ph H F H H HH CF₃ H CF₃ A-192 Ph H CN H H H H F H CF₃ A-193 Ph H H H H HSi(CH₃)₂C₆F₁₃ H H CF₃ A-194 Ph H F H H H F CN H CF₃ A-195 Ph H C₆F₅ H HH H F H CF₃ A-196 Ph H C₆F₅ H H H H CF₃ H CF₃ A-197 Ph H C₆F₅ H H H C₆F₅H H CF₃ A-198 Ph H C₆F₅ H H H H C₆F₅ H CF₃ A-199 Ph H H C₆F₅ H H C₆F₅ HH CF₃ A-200 Ph H H C₆F₅ H H H C₆F₅ H CF₃ A-201 Ph H H OCH₃ H F H F H CF₃A-202 Ph H H OCH₃ H F CN F H CF₃ A-203 Ph H H OCH₃ H CF₃ H CF₃ H CF₃A-204 Ph H H N(CH₃)₂ H F H F H CF₃ A-205 Ph H H N(CH₃)₂ H F CN F H CF₃A-206 Ph H H N(CH₃)₂ H CF₃ H CF₃ H CF₃ A-207 Ph ¹⁾ ¹⁾ H H H H H H CF₃A-208 Ph ¹⁾ ¹⁾ H H H H CH₃ H CF₃ A-209 Ph ¹⁾ ¹⁾ H H H H OCH₃ H CF₃ A-210Ph ¹⁾ ¹⁾ H H H H N(CH₃)₂ H CF₃ A-211 Ph ¹⁾ ¹⁾ H H H CH₃ H H CF₃ A-212 Ph¹⁾ ¹⁾ H H H OCH₃ H H CF₃ A-213 Ph ¹⁾ ¹⁾ H H H N(CH₃)₂ H H CF₃ A-214 Ph HH ¹⁾ ¹⁾ H H H H CF₃ A-215 Ph H H ¹⁾ ¹⁾ H H CH₃ H CF₃ A-216 Ph H H ¹⁾ ¹⁾H H OCH₃ H CF₃ A-217 Ph H H ¹⁾ ¹⁾ H H N(CH₃)₂ H CF₃ A-218 Ph H H ¹⁾ ¹⁾ HCH₃ H H CF₃ A-219 Ph H H ¹⁾ ¹⁾ H OCH₃ H H CF₃ A-210 Ph H H ¹⁾ ¹⁾ HN(CH₃)₂ H H CF₃ A-211 Ph H H H H H H H H ²⁾ A-212 Ph H H H H H H CH₃ H²⁾ A-213 Ph H H H H H H Ph H ²⁾ A-214 Ph H H H H H H t-Bu H ²⁾ A-215 PhH H H H H H C₆H₁₁ H ²⁾ A-216 Ph H H H H H H F H ²⁾ A-217 Ph H H H H H HOCH₃ H ²⁾ A-218 Ph H H H H H H OC₆H₅ H ²⁾ A-219 Ph H H H H H H OH H ²⁾A-220 Ph H H H H H H OCF₃ H ²⁾ A-221 Ph H H H H H H OSi(CH₃)₂C(CH₃)₃ H²⁾ A-222 Ph H H H H H H CF₃ H ²⁾ A-223 Ph H H H H H H SCH₃ H ²⁾ A-224 PhH H H H H H SO₂CH₃ H ²⁾ A-225 Ph H H H H H H SOCH₃ H ²⁾ A-226 Ph H H H HH H SH H ²⁾ A-227 Ph H H H H H H NO₂ H ²⁾ A-228 Ph H H H H H H N(CH₃)₂ H²⁾ A-229 Ph H H H H H H NH₂ H ²⁾ A-230 Ph H H H H H H NCOCH₃ H ²⁾ A-231Ph H H H H H H NSO₂CH₃ H ²⁾ A-232 Ph H H H H H H HNCH₂CH₃ H ²⁾ A-233 PhH H H H H H CHO H ²⁾ A-234 Ph H H H H H H CH₂OH H ²⁾ A-235 Ph H H H H HH CH₂Br H ²⁾ A-236 Ph H H H H H H CH₂CN H ²⁾ A-237 Ph H H H H H HCH₂CO₂H H ²⁾ A-238 Ph H H H H H H CH₂OCH₃ H ²⁾ A-239 Ph H H H H H HCH₂N(CH₂CH₃)₂ H ²⁾ A-240 Ph H H H H H H CHCHCO₂CH₃ H ²⁾ A-241 Ph H H H HH H CH₂CH₂CO₂CH₃ H ²⁾ A-242 Ph H H H H H H C₆F₅ H ²⁾ A-243 Ph H H H H HH H CH₃ ²⁾ A-244 Ph H H H H H CH₃ H H ²⁾ A-245 Ph H H H H H H H CHCH₂ ²⁾A-246 Ph H H H H H CHCH₂ H H ²⁾ A-247 Ph H H H H H H H Ph ²⁾ A-248 Ph HH H H H Ph H H ²⁾ A-249 Ph H H H H H C₆F₅ H H ²⁾ A-250 Ph H H H H H CF₃H CF₃ ²⁾ A-251 Ph H H H H H H H CF₃ ²⁾ A-252 Ph H H H H H CF₃ H H ²⁾A-253 Ph H H H H H F H H ²⁾ A-254 Ph H H H H H H H F ²⁾ A-255 Ph H H H HH F H F ²⁾ A-256 Ph H H H H H H H OCF₃ ²⁾ A-257 Ph H H H H H OCF₃ H H ²⁾A-258 Ph H H H H H NO₂ H CF₃ ²⁾ A-259 Ph H H H H H CF₃ H NO₂ ²⁾ A-260 PhH H H H H CN H H ²⁾ A-261 Ph H H H H H H H CN ²⁾ A-252 Ph H H H H H H HSi(CH₃)₃ ²⁾ A-263 Ph H H H H H Si(CH₃)₃ H H ²⁾ A-264 Ph H H H H H NO₂ HCN ²⁾ A-265 Ph H H H H H CN H NO₂ ²⁾ A-266 Ph CF₃ H H H H H H H ²⁾ A-267Ph Cl H H H H H H H ²⁾ A-268 Ph NO₂ H H H H H H H ²⁾ A-269 Ph CN H H H HH H H ²⁾ A-270 Ph CH₃ H H H H H H H ²⁾ A-271 Ph OCH₃ H H H H H H H ²⁾A-272 Ph Ph H H H H H H H ²⁾ A-273 Ph F H H H H H H H ²⁾ A-274 Ph H H HCF₃ H H H H ²⁾ A-275 Ph H H H CN H H H H ²⁾ A-276 Ph H H H NO₂ H H H H²⁾ A-277 Ph H H H CH₃ H H H H ²⁾ A-278 Ph H H H Ph H H H H ²⁾ A-279 Ph HH H F H H H H ²⁾ A-280 Ph H H H OCH₃ H H H H ²⁾ A-281 Ph H H CF₃ H H H HH ²⁾ A-282 Ph H H CH₃ H H H H H ²⁾ A-283 Ph H CF₃ H H H H H H ²⁾ A-284Ph H CH₃ H H H H H H ²⁾ A-285 Ph H F H H H H H H ²⁾ A-286 Ph H C₆F₅ H HH H H H ²⁾ A-287 Ph H H C₆F₅ H H H H H ²⁾ A-288 Ph H C₆H₅ H H H H H H ²⁾A-289 Ph H H C₆H₅ H H H H H ²⁾ A-290 Ph H CF₃ H H H H F H ²⁾ A-291 Ph HF H H H H CF₃ H ²⁾ A-292 Ph H CN H H H H F H ²⁾ A-293 Ph H H H H HSi(CH₃)₂C₆F₅ H H ²⁾ A-294 Ph H F H H H F CN H ²⁾ A-295 Ph H C₆F₅ H H H HF H ²⁾ A-296 Ph H C₆F₅ H H H H CF₃ H ²⁾ A-297 Ph H C₆F₅ H H H C₆F₅ H H²⁾ A-298 Ph H C₆F₅ H H H H C₆F₅ H ²⁾ A-299 Ph H H C₆F₅ H H C₆F₅ H H ²⁾A-300 Ph H H C₆F₅ H H H C₆F₅ H ²⁾ A-301 Ph H H OCH₃ H F H F H ²⁾ A-302Ph H H OCH₃ H F CN F H ²⁾ A-303 Ph H H OCH₃ H CF₃ H CF₃ H ²⁾ A-304 Ph HH N(CH₃)₂ H F H F H ²⁾ A-305 Ph H H N(CH₃)₂ H F CN F H ²⁾ A-306 Ph H HN(CH₃)₂ H CF₃ H CF₃ H ²⁾ A-307 Ph ¹⁾ ¹⁾ H H H H H H ²⁾ A-308 Ph ¹⁾ ¹⁾ HH H H CH₃ H ²⁾ A-309 Ph ¹⁾ ¹⁾ H H H H OCH₃ H ²⁾ A-310 Ph ¹⁾ ¹⁾ H H H HN(CH₃)₂ H ²⁾ A-311 Ph ¹⁾ ¹⁾ H H H CH₃ H H ²⁾ A-312 Ph ¹⁾ ¹⁾ H H H OCH₃ HH ²⁾ A-313 Ph ¹⁾ ¹⁾ H H H N(CH₃)₂ H H ²⁾ A-314 Ph H H ¹⁾ ¹⁾ H H H H ²⁾A-315 Ph H H ¹⁾ ¹⁾ H H CH₃ H ²⁾ A-316 Ph H H ¹⁾ ¹⁾ H H OCH₃ H ²⁾ A-317Ph H H ¹⁾ ¹⁾ H H N(CH₃)₂ H ²⁾ A-318 Ph H H ¹⁾ ¹⁾ H CH₃ H H ²⁾ A-319 Ph HH ¹⁾ ¹⁾ H OCH₃ H H ²⁾ A-320 Ph H H ¹⁾ ¹⁾ H N(CH₃)₂ H H ²⁾

Cpd. R⁵ R⁶ R⁷ R⁸ R⁹ A¹⁰ A¹¹ A¹² A¹³ Z¹ A′-1 Ph H H H H H H H H Ph A′-2Ph H H H H H H CH₃ H Ph A′-3 Ph H H H H H H Ph H Ph A′-4 Ph H H H H H Ht-Bu H Ph A′-5 Ph H H H H H H C₆H₁₁ H Ph A′-6 Ph H H H H H H F H Ph A′-7Ph H H H H H H OCH₃ H Ph A′-8 Ph H H H H H H OC₆H₅ H Ph A′-9 Ph H H H HH H OH H Ph A′-10 Ph H H H H H H OCF₃ H Ph A′-11 Ph H H H H H HOSi(CH₃)₂C(CH₃)₃ H Ph A′-12 Ph H H H H H H CF₃ H Ph A′-13 Ph H H H H H HSCH₃ H Ph A′-14 Ph H H H H H H SO₂CH₃ H Ph A′-15 Ph H H H H H H SOCH₃ HPh A′-16 Ph H H H H H H SH H Ph A′-17 Ph H H H H H H NO₂ H Ph A′-18 Ph HH H H H H N(CH₃)₂ H Ph A′-19 Ph H H H H H H NH₂ H Ph A′-20 Ph H H H H HH NCOCH₃ H Ph A′-21 Ph H H H H H H NSO₂CH₃ H Ph A′-22 Ph H H H H H HHNCH₂CH₃ H Ph A′-23 Ph H H H H H H CHO H Ph A′-24 Ph H H H H H H CH₂OH HPh A′-25 Ph H H H H H H CH₂Br H Ph A′-26 Ph H H H H H H CH₂CN H Ph A′-27Ph H H H H H H CH₂CO₂H H Ph A′-28 Ph H H H H H H CH₂OCH₃ H Ph A′-29 Ph HH H H H H CH₂N(CH₂CH₃)₂ H Ph A′-30 Ph H H H H H H CHCHCO₂CH₃ H Ph A′-31Ph H H H H H H CH₂CH₂CO₂CH₃ H Ph A′-32 Ph H H H H H H C₆F₅ H Ph A′-33 PhH H H H H H H CH₃ Ph A′-34 Ph H H H H H CH₃ H H Ph A′-35 Ph H H H H H HH CHCH₂ Ph A′-36 Ph H H H H H CHCH₂ H H Ph A′-37 Ph H H H H H H H Ph PhA′-38 Ph H H H H H Ph H H Ph A′-39 Ph H H H H H C₆F₅ H H Ph A′-40 Ph H HH H H CF₃ H CF₃ Ph A′-41 Ph H H H H H H H CF₃ Ph A′-42 Ph H H H H H CF₃H H Ph A′-43 Ph H H H H H F H H Ph A′-44 Ph H H H H H H H F Ph A′-45 PhH H H H H F H F Ph A′-46 Ph H H H H H H H OCF₃ Ph A′-47 Ph H H H H HOCF₃ H H Ph A′-48 Ph H H H H H NO₂ H CF₃ Ph A′-49 Ph H H H H H CF₃ H NO₂Ph A′-50 Ph H H H H H CN H H Ph A′-51 Ph H H H H H H H CN Ph A′-52 Ph HH H H H H H Si(CH₃)₃ Ph A′-53 Ph H H H H H Si(CH₃)₃ H H Ph A′-54 Ph H HH H H NO₂ H CN Ph A′-55 Ph H H H H H CN H NO₂ Ph A′-56 Ph CF₃ H H H H HH H Ph A′-57 Ph Cl H H H H H H H Ph A′-58 Ph NO₂ H H H H H H H Ph A′-59Ph CN H H H H H H H Ph A′-60 Ph CH₃ H H H H H H H Ph A′-61 Ph OCH₃ H H HH H H H Ph A′-62 Ph Ph H H H H H H H Ph A′-63 Ph F H H H H H H H PhA′-64 Ph H H H CF₃ H H H H Ph A′-65 Ph H H H CN H H H H Ph A′-66 Ph H HH NO₂ H H H H Ph A′-67 Ph H H H CH₃ H H H H Ph A′-68 Ph H H H Ph H H H HPh A′-69 Ph H H H F H H H H Ph A′-70 Ph H H H OCH₃ H H H H Ph A′-71 Ph HH CF₃ H H H H H Ph A′-72 Ph H H CH₃ H H H H H Ph A′-73 Ph H CF₃ H H H HH H Ph A′-74 Ph H CH₃ H H H H H H Ph A′-75 Ph H F H H H H H H Ph A′-76Ph H C₆F₅ H H H H H H Ph A′-77 Ph H H C₆F₅ H H H H H Ph A′-78 Ph H C₆H₅H H H H H H Ph A′-79 Ph H H C₆H₅ H H H H H Ph A′-80 Ph H CF₃ H H H H F HPh A′-81 Ph H F H H H H CF₃ H Ph A′-82 Ph H CN H H H H F H Ph A′-83 Ph HH H H H Si(CH₃)₂ C₆F₁₃ H H Ph A′-84 Ph H F H H H F CN H Ph A′-85 Ph HC₆F₅ H H H H F H Ph A′-86 Ph H C₆F₅ H H H H CF₃ H Ph A′-87 Ph H C₆F₅ H HH C₆F₅ H H Ph A′-88 Ph H C₆F₅ H H H H C₆F₅ H Ph A′-89 Ph H H C₆F₅ H HC₆F₅ H H Ph A′-90 Ph H H C₆F₅ H H H C₆F₅ H Ph A′-91 Ph H H OCH₃ H F H FH Ph A′-92 Ph H H OCH₃ H F CN F H Ph A′-93 Ph H H OCH₃ H CF₃ H CF₃ H PhA′-94 Ph H H N(CH₃)₂ H F H F H PH A′-95 Ph H H N(CH₃)₂ H F CN F H PhA′-96 Ph H H N(CH₃)₂ H CF₃ H CF₃ H Ph A′-97 Ph ¹⁾ ¹⁾ H H H H H H PhA′-98 Ph ¹⁾ ¹⁾ H H H H CH₃ H Ph A′-99 Ph ¹⁾ ¹⁾ H H H H OCH₃ H Ph A′-100Ph ¹⁾ ¹⁾ H H H H N(CH₃)₂ H Ph A′-101 Ph ¹⁾ ¹⁾ H H H CH₃ H H Ph A′-102 Ph¹⁾ ¹⁾ H H H OCH₃ H H Ph A′-103 Ph ¹⁾ ¹⁾ H H H N(CH₃)₂ H H Ph A′-104 Ph HH ¹⁾ ¹⁾ H H H H Ph A′-105 Ph H H ¹⁾ ¹⁾ H H CH₃ H Ph A′-106 Ph H H ¹⁾ ¹⁾H H OCH₃ H Ph A′-107 Ph H H ¹⁾ ¹⁾ H H N(CH₃)₂ H Ph A′-108 Ph H H ¹⁾ ¹⁾ HCH₃ H H Ph A′-109 Ph H H ¹⁾ ¹⁾ H OCH₃ H H Ph A′-110 Ph H H ¹⁾ ¹⁾ HN(CH₃)₂ H H Ph A′-111 Ph H H H H H H H H CF₃ A′-112 Ph H H H H H H CH₃ HCF₃ A′-113 Ph H H H H H H Ph H CF₃ A′-114 Ph H H H H H H t-Bu H CF₃A′-115 Ph H H H H H H C₆H₁₁ H CF₃ A′-116 Ph H H H H H H F H CF₃ A′-117Ph H H H H H H OCH₃ H CF₃ A′-118 Ph H H H H H H OC₆H₅ H CF₃ A′-119 Ph HH H H H H OH H CF₃ A′-120 Ph H H H H H H OCF₃ H CF₃ A′-121 Ph H H H H HH OSi(CH₃)₂C(CH₃)₃ H CF₃ A′-122 Ph H H H H H H CF₃ H CF₃ A′-123 Ph H H HH H H SCH₃ H CF₃ A′-124 Ph H H H H H H SO₂CH₃ H CF₃ A′-125 Ph H H H H HH SOCH₃ H CF₃ A′-126 Ph H H H H H H SH H CF₃ A′-127 Ph H H H H H H NO₂ HCF₃ A′-128 Ph H H H H H H N(CH₃)₂ H CF₃ A′-129 Ph H H H H H H NH₂ H CF₃A′-130 Ph H H H H H H NCOCH₃ H CF₃ A′-131 Ph H H H H H H NSO₂CH₃ H CF₃A′-132 Ph H H H H H H HNCH₂CH₃ H CF₃ A′-133 Ph H H H H H H CHO H CF₃A′-134 Ph H H H H H H CH₂OH H CF₃ A′-135 Ph H H H H H H CH₂Br H CF₃A′-136 Ph H H H H H H CH₂CN H CF₃ A′-137 Ph H H H H H H CH₂CO₂H H CF₃A′-138 Ph H H H H H H CH₂OCH₃ H CF₃ A′-139 Ph H H H H H H CH₂N(CH₂CH₃)₂H CF₃ A′-140 Ph H H H H H H CHCHCO₂CH₃ H CF₃ A′-141 Ph H H H H H HCH₂CH₂CO₂CH₃ H CF₃ A′-142 Ph H H H H H H C₆F₅ H CF₃ A′-143 Ph H H H H HH H CH₃ CF₃ A′-144 Ph H H H H H CH₃ H H CF₃ A′-145 Ph H H H H H H HCHCH₂ CF₃ A′-146 Ph H H H H H CHCH₂ H H CF₃ A′-147 Ph H H H H H H H PhCF₃ A′-148 Ph H H H H H Ph H H CF₃ A′-149 Ph H H H H H C₆F₅ H H CF₃A′-150 Ph H H H H H CF₃ H CF₃ CF₃ A′-151 Ph H H H H H H H CF₃ CF₃ A′-152Ph H H H H H CF₃ H H CF₃ A′-153 Ph H H H H H F H H CF₃ A′-154 Ph H H H HH H H F CF₃ A′-155 Ph H H H H H F H F CF₃ A′-156 Ph H H H H H H H OCF₃CF₃ A′-157 Ph H H H H H OCF₃ H H CF₃ A′-158 Ph H H H H H NO₂ H CF₃ CF₃A′-159 Ph H H H H H CF₃ H NO₂ CF₃ A′-160 Ph H H H H H CN H H CF₃ A′-161Ph H H H H H H H CN CF₃ A′-162 Ph H H H H H H H Si(CH₃)₃ CF₃ A′-163 Ph HH H H H Si(CH₃)₃ H H CF₃ A′-164 Ph H H H H H NO₂ H CN CF₃ A′-165 Ph H HH H H CN H NO₂ CF₃ A′-166 Ph CF₃ H H H H H H H CF₃ A′-167 Ph Cl H H H HH H H CF₃ A′-168 Ph NO₂ H H H H H H H CF₃ A′-169 Ph CN H H H H H H H CF₃A′-170 Ph CH₃ H H H H H H H CF₃ A′-171 Ph OCH₃ H H H H H H H CF₃ A′-172Ph Ph H H H H H H H CF₃ A′-173 Ph F H H H H H H H CF₃ A′-174 Ph H H HCF₃ H H H H CF₃ A′-175 Ph H H H CN H H H H CF₃ A′-176 Ph H H H NO₂ H H HH CF₃ A′-177 Ph H H H CH₃ H H H H CF₃ A′-178 Ph H H H Ph H H H H CF₃A′-179 Ph H H H F H H H H CF₃ A′-180 Ph H H H OCH₃ H H H H CF₃ A′-181 PhH H CF₃ H H H H H CF₃ A′-182 Ph H H CH₃ H H H H H CF₃ A′-183 Ph H CF₃ HH H H H H CF₃ A′-184 Ph H CH₃ H H H H H H CF₃ A′-185 Ph H F H H H H H HCF₃ A′-186 Ph H C₆F₅ H H H H H H CF₃ A′-187 Ph H H C₆F₅ H H H H H CF₃A′-188 Ph H C₆H₅ H H H H H H CF₃ A′-189 Ph H H C₆H₅ H H H H H CF₃ A′-190Ph H CF₃ H H H H F H CF₃ A′-191 Ph H F H H H H CF₃ H CF₃ A′-192 Ph H CNH H H H F H CF₃ A′-193 Ph H H H H H Si(CH₃)₂C₆F₁₃ H H CF₃ A′-194 Ph H FH H H F CN H CF₃ A′-195 Ph H C₆F₅ H H H H F H CF₃ A′-196 Ph H C₆F₅ H H HH CF₃ H CF₃ A′-197 Ph H C₆F₅ H H H C₆F₅ H H CF₃ A′-198 Ph H C₆F₅ H H H HC₆F₅ H CF₃ A′-199 Ph H H C₆F₅ H H C₆F₅ H H CF₃ A′-200 Ph H H C₆F₅ H H HC₆F₅ H CF₃ A′-201 Ph H H OCH₃ H F H F H CF₃ A′-202 Ph H H OCH₃ H F CN FH CF₃ A′-203 Ph H H OCH₃ H CF₃ H CF₃ H CF₃ A′-204 Ph H H N(CH₃)₂ H F H FH CF₃ A′-205 Ph H H N(CH₃)₂ H F CN F H CF₃ A′-206 Ph H H N(CH₃)₂ H CF₃ HCF₃ H CF₃ A′-207 Ph ¹⁾ ¹⁾ H H H H H H CF₃ A′-208 Ph ¹⁾ ¹⁾ H H H H CH₃ HCF₃ A′-209 Ph ¹⁾ ¹⁾ H H H H OCH₃ H CF₃ A′-210 Ph ¹⁾ ¹⁾ H H H H N(CH₃)₂ HCF₃ A′-211 Ph ¹⁾ ¹⁾ H H H CH₃ H H CF₃ A′-212 Ph ¹⁾ ¹⁾ H H H OCH₃ H H CF₃A′-213 Ph ¹⁾ ¹⁾ H H H N(CH₃)₂ H H CF₃ A′-214 Ph H H ¹⁾ ¹⁾ H H H H CF₃A′-215 Ph H H ¹⁾ ¹⁾ H H CH₃ H CF₃ A′-216 Ph H H ¹⁾ ¹⁾ H H OCH₃ H CF₃A′-217 Ph H H ¹⁾ ¹⁾ H H N(CH₃)₂ H CF₃ A′-218 Ph H H ¹⁾ ¹⁾ H CH₃ H H CF₃A′-219 Ph H H ¹⁾ ¹⁾ H OCH₃ H H CF₃ A′-210 Ph H H ¹⁾ ¹⁾ H N(CH₃)₂ H H CF₃A′-211 Ph H H H H H H H H ²⁾ A′-212 Ph H H H H H H CH₃ H ²⁾ A′-213 Ph HH H H H H Ph H ²⁾ A′-214 Ph H H H H H H t-Bu H ²⁾ A′-215 Ph H H H H H HC₆H₁₁ H ²⁾ A′-216 Ph H H H H H H F H ²⁾ A′-217 Ph H H H H H H OCH₃ H ²⁾A′-218 Ph H H H H H H OC₆H₅ H ²⁾ A′-219 Ph H H H H H H OH H ²⁾ A′-220 PhH H H H H H OCF₃ H ²⁾ A′-221 Ph H H H H H H OSi(CH₃)₂C(CH₃)₃ H ²⁾ A′-222Ph H H H H H H CF₃ H ²⁾ A′-223 Ph H H H H H H SCH₃ H ²⁾ A′-224 Ph H H HH H H SO₂CH₃ H ²⁾ A′-225 Ph H H H H H H SOCH₃ H ²⁾ A′-226 Ph H H H H H HSH H ²⁾ A′-227 Ph H H H H H H NO₂ H ²⁾ A′-228 Ph H H H H H H N(CH₃)₂ H²⁾ A′-229 Ph H H H H H H NH₂ H ²⁾ A′-230 Ph H H H H H H NCOCH₃ H ²⁾A′-231 Ph H H H H H H NSO₂CH₃ H ²⁾ A′-232 Ph H H H H H H HNCH₂CH₃ H ²⁾A′-233 Ph H H H H H H CHO H ²⁾ A′-234 Ph H H H H H H CH₂OH H ²⁾ A′-235Ph H H H H H H CH₂Br H ²⁾ A′-236 Ph H H H H H H CH₂CN H ²⁾ A′-237 Ph H HH H H H CH₂CO₂H H ²⁾ A′-238 Ph H H H H H H CH₂OCH₃ H ²⁾ A′-239 Ph H H HH H H CH₂N(CH₂CH₃)₂ H ²⁾ A′-240 Ph H H H H H H CHCHCO₂CH₃ H ²⁾ A′-241 PhH H H H H H CH₂CH₂CO₂CH₃ H ²⁾ A′-242 Ph H H H H H H C₆F₅ H ²⁾ A′-243 PhH H H H H H H CH₃ ²⁾ A′-244 Ph H H H H H CH₃ H H ²⁾ A′-245 Ph H H H H HH H CHCH₂ ²⁾ A′-246 Ph H H H H H CHCH₂ H H ²⁾ A′-247 Ph H H H H H H H Ph²⁾ A′-248 Ph H H H H H Ph H H ²⁾ A′-249 Ph H H H H H C₆F₅ H H ²⁾ A′-250Ph H H H H H CF₃ H CF₃ ²⁾ A′-251 Ph H H H H H H H CF₃ ²⁾ A′-252 Ph H H HH H CF₃ H H ²⁾ A′-253 Ph H H H H H F H H ²⁾ A′-254 Ph H H H H H H H F ²⁾A′-255 Ph H H H H H F H F ²⁾ A′-256 Ph H H H H H H H OCF₃ ²⁾ A′-257 Ph HH H H H OCF₃ H H ²⁾ A′-258 Ph H H H H H NO₂ H CF₃ ²⁾ A′-259 Ph H H H H HCF₃ H NO₂ ²⁾ A′-260 Ph H H H H H CN H H ²⁾ A′-261 Ph H H H H H H H CN ²⁾A′-252 Ph H H H H H H H Si(CH₃)₃ ²⁾ A′-263 Ph H H H H H Si(CH₃)₃ H H ²⁾A′-264 Ph H H H H H NO₂ H CN ²⁾ A′-265 Ph H H H H H CN H NO₂ ²⁾ A′-266Ph CF₃ H H H H H H H ²⁾ A′-267 Ph Cl H H H H H H H ²⁾ A′-268 Ph NO₂ H HH H H H H ²⁾ A′-269 Ph CN H H H H H H H ²⁾ A′-270 Ph CH₃ H H H H H H H²⁾ A′-271 Ph OCH₃ H H H H H H H ²⁾ A′-272 Ph Ph H H H H H H H ²⁾ A′-273Ph F H H H H H H H ²⁾ A′-274 Ph H H H CF₃ H H H H ²⁾ A′-275 Ph H H H CNH H H H ²⁾ A′-276 Ph H H H NO₂ H H H H ²⁾ A′-277 Ph H H H CH₃ H H H H ²⁾A′-278 Ph H H H Ph H H H H ²⁾ A′-279 Ph H H H F H H H H ²⁾ A′-280 Ph H HH OCH₃ H H H H ²⁾ A′-281 Ph H H CF₃ H H H H H ²⁾ A′-282 Ph H H CH₃ H H HH H ²⁾ A′-283 Ph H CF₃ H H H H H H ²⁾ A′-284 Ph H CH₃ H H H H H H ²⁾A′-285 Ph H F H H H H H H ²⁾ A′-286 Ph H C₆F₅ H H H H H H ²⁾ A′-287 Ph HH C₆F₅ H H H H H ²⁾ A′-288 Ph H C₆H₅ H H H H H H ²⁾ A′-289 Ph H H C₆H₅ HH H H H ²⁾ A′-290 Ph H CF₃ H H H H F H ²⁾ A′-291 Ph H F H H H H CF₃ H ²⁾A′-292 Ph H CN H H H H F H ²⁾ A′-293 Ph H H H H H Si(CH₃)₂C₆F₅ H H ²⁾A′-294 Ph H F H H H F CN H ²⁾ A′-295 Ph H C₆F₅ H H H H F H ²⁾ A′-296 PhH C₆F₅ H H H H CF₃ H ²⁾ A′-297 Ph H C₆F₅ H H H C₆F₅ H H ²⁾ A′-298 Ph HC₆F₅ H H H H C₆F₅ H ²⁾ A′-299 Ph H H C₆F₅ H H C₆F₅ H H ²⁾ A′-300 Ph H HC₆F₅ H H H C₆F₅ H ²⁾ A′-301 Ph H H OCH₃ H F H F H ²⁾ A′-302 Ph H H OCH₃H F CN F H ²⁾ A′-303 Ph H H OCH₃ H CF₃ H CF₃ H ²⁾ A′-304 Ph H H N(CH₃)₂H F H F H ²⁾ A′-305 Ph H H N(CH₃)₂ H F CN F H ²⁾ A′-306 Ph H H N(CH₃)₂ HCF₃ H CF₃ H ²⁾ A′-307 Ph ¹⁾ ¹⁾ H H H H H H ²⁾ A′-308 Ph ¹⁾ ¹⁾ H H H HCH₃ H ²⁾ A′-309 Ph ¹⁾ ¹⁾ H H H H OCH₃ H ²⁾ A′-310 Ph ¹⁾ ¹⁾ H H H HN(CH₃)₂ H ²⁾ A′-311 Ph ¹⁾ ¹⁾ H H H CH₃ H H ²⁾ A′-312 Ph ¹⁾ ¹⁾ H H H OCH₃H H ²⁾ A′-313 Ph ¹⁾ ¹⁾ H H H N(CH₃)₂ H H ²⁾ A′-314 Ph H H ¹⁾ ¹⁾ H H H H²⁾ A′-315 Ph H H ¹⁾ ¹⁾ H H CH₃ H ²⁾ A′-316 Ph H H ¹⁾ ¹⁾ H H OCH₃ H ²⁾A′-317 Ph H H ¹⁾ ¹⁾ H H N(CH₃)₂ H ²⁾ A′-318 Ph H H ¹⁾ ¹⁾ H CH₃ H H ²⁾A′-319 Ph H H ¹⁾ ¹⁾ H OCH₃ H H ²⁾ A′-320 Ph H H ¹⁾ ¹⁾ H N(CH₃)₂ H H ²⁾

Cpd. R⁵ R⁶ R⁷ R⁸ R⁹ A¹⁰ A¹¹ A¹² A¹³ Z¹ = Z² B-1 Ph H H H H H H H H H B-2Ph H H H H H H CH₃ H H B-3 Ph H H H H H H Ph H H B-4 Ph H H H H H H t-BuH H B-5 Ph H H H H H H C₆H₁₁ H H B-6 Ph H H H H H H F H H B-7 Ph H H H HH H OCH₃ H H B-8 Ph H H H H H H OC₆H₅ H H B-9 Ph H H H H H H OH H H B-10Ph H H H H H H OCF₃ H H B-11 Ph H H H H H H OSi(CH₃)₂C(CH₃)₃ H H B-12 PhH H H H H H CF₃ H H B-13 Ph H H H H H H SCH₃ H H B-14 Ph H H H H H HSO₂CH₃ H H B-15 Ph H H H H H H SOCH₃ H H B-16 Ph H H H H H H SH H H B-17Ph H H H H H H NO₂ H H B-18 Ph H H H H H H N(CH₃)₂ H H B-19 Ph H H H H HH NH₂ H H B-20 Ph H H H H H H NCOCH₃ H H B-21 Ph H H H H H H NSO₂CH₃ H HB-22 Ph H H H H H H HNCH₂CH₃ H H B-23 Ph H H H H H H CHO H H B-24 Ph H HH H H H CH₂OH H H B-25 Ph H H H H H H CH₂Br H H B-26 Ph H H H H H HCH₂CN H H B-27 Ph H H H H H H CH₂CO₂H H H B-28 Ph H H H H H H CH₂OCH₃ HH B-29 Ph H H H H H H CH₂N(CH₂CH₃)₂ H H B-30 Ph H H H H H H CHCHCO₂CH₃ HH B-31 Ph H H H H H H CH₂CH₂CO₂CH₃ H H B-32 Ph H H H H H H C₆F₅ H H B-33Ph H H H H H H H CH₃ H B-34 Ph H H H H H CH₃ H H H B-35 Ph H H H H H H HCHCH₂ H B-36 Ph H H H H H CHCH₂ H H H B-37 Ph H H H H H H H Ph H B-38 PhH H H H H Ph H H H B-39 Ph H H H H H C₆F₅ H H H B-40 Ph H H H H H CF₃ HCF₃ H B-41 Ph H H H H H H H CF₃ H B-42 Ph H H H H H CF₃ H H H B-43 Ph HH H H H F H H H B-44 Ph H H H H H H H F H B-45 Ph H H H H H F H F H B-46Ph H H H H H H H OCF₃ H B-47 Ph H H H H H OCF₃ H H H B-48 Ph H H H H HNO₂ H CF₃ H B-49 Ph H H H H H CF₃ H NO₂ H B-50 Ph H H H H H CN H H HB-51 Ph H H H H H H H CN H B-52 Ph H H H H H H H Si(CH₃)₃ H B-53 Ph H HH H H Si(CH₃)₃ H H H B-54 Ph H H H H H NO₂ H CN H B-55 Ph H H H H H CN HNO₂ H B-56 Ph CF₃ H H H H H H H H B-57 Ph Cl H H H H H H H H B-58 Ph NO₂H H H H H H H H B-59 Ph CN H H H H H H H H B-60 Ph CH₃ H H H H H H H HB-61 Ph OCH₃ H H H H H H H H B-62 Ph Ph H H H H H H H H B-63 Ph F H H HH H H H H B-64 Ph H H H CF₃ H H H H H B-65 Ph H H H CN H H H H H B-66 PhH H H NO₂ H H H H H B-67 Ph H H H CH₃ H H H H H B-68 Ph H H H Ph H H H HH B-69 Ph H H H F H H H H H B-70 Ph H H H OCH₃ H H H H H B-71 Ph H H CF₃H H H H H H B-72 Ph H H CH₃ H H H H H H B-73 Ph H CF₃ H H H H H H H B-74Ph H CH₃ H H H H H H H B-75 Ph H F H H H H H H H B-76 Ph H C₆F₅ H H H HH H H B-77 Ph H H C₆F₅ H H H H H H B-78 Ph H C₆H₅ H H H H H H H B-79 PhH H C₆H₅ H H H H H H B-80 Ph H H OCH₃ H F H F H H B-81 Ph H CF₃ H H H HF H H B-82 Ph H H ¹⁾ ¹⁾ H H H H H B-83 Ph H H H H H Si(CH₃)₂C₆F₁₃ H H HB-84 CH₃ H H H H H H H H H B-85 Ph H C₆F₅ H H H H F H H B-86 Ph H C₆F₅ HH H H CF₃ H H B-87 Ph H C₆F₅ H H H C₆F₅ H H H B-88 Ph H C₆F₅ H H H HC₆F₅ H H B-89 Ph H H C₆F₅ H H C₆F₅ H H H B-90 Ph H H C₆F₅ H H H C₆F₅ H HB-91 Ph H H OCH₃ H F H F H H B-92 Ph H H OCH₃ H F CN F H H B-93 Ph H HOCH₃ H CF₃ H CF₃ H H B-94 Ph H H N(CH₃)₂ H F H F H H B-95 Ph H H N(CH₃)₂H F CN F H H B-96 Ph H H N(CH₃)₂ H CF₃ H CF₃ H H B-97 Ph ¹⁾ ¹⁾ H H H H HH H B-98 Ph ¹⁾ ¹⁾ H H H H CH₃ H H B-99 Ph ¹⁾ ¹⁾ H H H H OCH₃ H H B-100Ph ¹⁾ ¹⁾ H H H H N(CH₃)₂ H H B-101 Ph ¹⁾ ¹⁾ H H H CH₃ H H H B-102 Ph ¹⁾¹⁾ H H H OCH₃ H H H B-103 Ph ¹⁾ ¹⁾ H H H N(CH₃)₂ H H H B-104 Ph H H ¹⁾¹⁾ H H H H H B-105 Ph H H ¹⁾ ¹⁾ H H CH₃ H H B-106 Ph H H ¹⁾ ¹⁾ H H OCH₃H H B-107 Ph H H ¹⁾ ¹⁾ H H N(CH₃)₂ H H B-108 Ph H H ¹⁾ ¹⁾ H CH₃ H H HB-109 Ph H H ¹⁾ ¹⁾ H OCH₃ H H H B-110 Ph H H ¹⁾ ¹⁾ H N(CH₃)₂ H H H

Cpd. R⁵ R⁶ R⁷ R⁸ R⁹ A¹¹ A¹² A¹³ Z¹ B′-1 Ph H H H H H H H Ph B′-2 Ph H HH H H CH₃ H Ph B′-3 Ph H H H H H Ph H Ph B′-4 Ph H H H H H t-Bu H PhB′-5 Ph H H H H H C₆H₁₁ H Ph B′-6 Ph H H H H H F H Ph B′-7 Ph H H H H HOCH₃ H Ph B′-8 Ph H H H H H OC₆H₅ H Ph B′-9 Ph H H H H H OH H Ph B′-10Ph H H H H H OCF₃ H Ph B′-11 Ph H H H H H OSi(CH₃)₂C(CH₃)₃ H Ph B′-12 PhH H H H H CF₃ H Ph B′-13 Ph H H H H H SCH₃ H Ph B′-14 Ph H H H H HSO₂CH₃ H Ph B′-15 Ph H H H H H SOCH₃ H Ph B′-16 Ph H H H H H SH H PhB′-17 Ph H H H H H NO₂ H Ph B′-18 Ph H H H H H N(CH₃)₂ H Ph B′-19 Ph H HH H H NH₂ H Ph B′-20 Ph H H H H H NCOCH₃ H Ph B′-21 Ph H H H H H NSO₂CH₃H Ph B′-22 Ph H H H H H HNCH₂CH₃ H Ph B′-23 Ph H H H H H CHO H Ph B′-24Ph H H H H H CH₂OH H Ph B′-25 Ph H H H H H CH₂Br H Ph B′-26 Ph H H H H HCH₂CN H Ph B′-27 Ph H H H H H CH₂CO₂H H Ph B′-28 Ph H H H H H CH₂OCH₃ HPh B′-29 Ph H H H H H CH₂N(CH₂CH₃)₂ H Ph B′-30 Ph H H H H H CHCHCO₂CH₃ HPh B′-31 Ph H H H H H CH₂CH₂CO₂CH₃ H Ph B′-32 Ph H H H H H C₆F₅ H PhB′-33 Ph H H H H H H CH₃ Ph B′-34 Ph H H H H CH₃ H H Ph B′-35 Ph H H H HH H CHCH₂ Ph B′-36 Ph H H H H CHCH₂ H H Ph B′-37 Ph H H H H H H Ph PhB′-38 Ph H H H H Ph H H Ph B′-39 Ph H H H H C₆F₅ H H Ph B′-40 Ph H H H HCF₃ H CF₃ Ph B′-41 Ph H H H H H H CF₃ Ph B′-42 Ph H H H H CF₃ H H PhB′-43 Ph H H H H F H H Ph B′-44 Ph H H H H H H F Ph B′-45 Ph H H H H F HF Ph B′-46 Ph H H H H H H OCF₃ Ph B′-47 Ph H H H H OCF₃ H H Ph B′-48 PhH H H H NO₂ H CF₃ Ph B′-49 Ph H H H H CF₃ H NO₂ Ph B′-50 Ph H H H H CN HH Ph B′-51 Ph H H H H H H CN Ph B′-52 Ph H H H H H H Si(CH₃)₃ Ph B′-53Ph H H H H Si(CH₃)₃ H H Ph B′-54 Ph H H H H NO₂ H CN Ph B′-55 Ph H H H HCN H NO₂ Ph B′-56 Ph CF₃ H H H H H H Ph B′-57 Ph Cl H H H H H H Ph B′-58Ph NO₂ H H H H H H Ph B′-59 Ph NO₂ H H H H H H Ph B′-60 Ph CH₃ H H H H HH Ph B′-61 Ph OCH₃ H H H H H H Ph B′-62 Ph Ph H H H H H H Ph B′-63 Ph FH H H H H H Ph B′-64 Ph H H H CF₃ H H H Ph B′-65 Ph H H H CN H H H PhB′-66 Ph H H H NO₂ H H H Ph B′-67 Ph H H H CH₃ H H H Ph B′-68 Ph H H HPh H H H Ph B′-69 Ph H H H F H H H Ph B′-70 Ph H H H OCH₃ H H H Ph B′-71Ph H H CF₃ H H H H Ph B′-72 Ph H H CH₃ H H H H Ph B′-73 Ph H CF₃ H H H HH Ph B′-74 Ph H CH₃ H H H H H Ph B′-75 Ph H F H H H H H Ph B′-76 Ph HC₆F₅ H H H H H Ph B′-77 Ph H H C₆F₅ H H H H Ph B′-78 Ph H C₆H₅ H H H H HPh B′-79 Ph H H C₆H₅ H H H H Ph

Cpd. R⁵ R⁶ R⁷ R⁸ R⁹ A¹⁰ A¹¹ A¹² A¹³ ¹⁾ C-1 Ph H H H H H H H H H C-2 Ph HH H H H H CH₃ H H C-3 Ph H H H H H H Ph H H C-4 Ph H H H H H H t-Bu H HC-5 Ph H H H H H H C₆H₁₁ H H C-6 Ph H H H H H H F H H C-7 Ph H H H H H HOCH₃ H H C-8 Ph H H H H H H OC₆H₅ H H C-9 Ph H H H H H H OH H H C-10 PhH H H H H H OCF₃ H H C-11 Ph H H H H H H OSi(CH₃)₂C(CH₃)₃ H H C-12 Ph HH H H H H CF₃ H H C-13 Ph H H H H H H SCH₃ H H C-14 Ph H H H H H HSO₂CH₃ H H C-15 Ph H H H H H H SOCH₃ H H C-16 Ph H H H H H H SH H H C-17Ph H H H H H H NO₂ H H C-18 Ph H H H H H H N(CH₃)₂ H H C-19 Ph H H H H HH NH₂ H H C-20 Ph H H H H H H NCOCH₃ H H C-21 Ph H H H H H H NSO₂CH₃ H HC-22 Ph H H H H H H HNCH₂CH₃ H H C-23 Ph H H H H H H CHO H H C-24 Ph H HH H H H CH₂OH H H C-25 Ph H H H H H H CH₂Br H H C-26 Ph H H H H H HCH₂CN H H C-27 Ph H H H H H H CH₂CO₂H H H C-28 Ph H H H H H H CH₂OCH₃ HH C-29 Ph H H H H H H CH₂N(CH₂CH₃)₂ H H C-30 Ph H H H H H H CHCHCO₂CH₃ HH C-31 Ph H H H H H H CH₂CH₂CO₂CH₃ H H C-32 Ph H H H H H H C₆F₅ H H C-33Ph H H H H H H H CH₃ H C-34 Ph H H H H H CH₃ H H H C-35 Ph H H H H H H HCHCH₂ H C-36 Ph H H H H H CHCH₂ H H H C-37 Ph H H H H H H H Ph H C-38 PhH H H H H Ph H H H C-39 Ph H H H H H C₆F₅ H H H C-40 Ph H H H H H CF₃ HCF₃ H C-41 Ph H H H H H H H CF₃ H C-42 Ph H H H H H CF₃ H H H C-43 Ph HH H H H F H H H C-44 Ph H H H H H H H F H C-45 Ph H H H H H F H F H C-46Ph H H H H H H H OCF₃ H C-47 Ph H H H H H OCF₃ H H H C-48 Ph H H H H HNO₂ H CF₃ H C-49 Ph H H H H H CF₃ H NO₂ H C-50 Ph H H H H H CN H H HC-51 Ph H H H H H H H CN H C-52 Ph H H H H H H H Si(CH₃)₃ H C-53 Ph H HH H H Si(CH₃)₃ H H H C-54 Ph H H H H H NO₂ H CN H C-55 Ph H H H H H CN HNO₂ H C-56 Ph CF₃ H H H H H H H H C-57 Ph Cl H H H H H H H H C-58 Ph NO₂H H H H H H H H C-59 Ph CN H H H H H H H H C-60 Ph CH₃ H H H H H H H HC-61 Ph OCH₃ H H H H H H H H C-62 Ph Ph H H H H H H H H C-63 Ph F H H HH H H H H C-64 Ph H H H CF₃ H H H H H C-65 Ph H H H CN H H H H H C-66 PhH H H NO₂ H H H H H C-67 Ph H H H CH₃ H H H H H C-68 Ph H H H Ph H H H HH C-69 Ph H H H F H H H H H C-70 Ph H H H OCH₃ H H H H H C-71 Ph H H CF₃H H H H H H C-72 Ph H H CH₃ H H H H H H C-73 Ph H CF₃ H H H H H H H C-74Ph H CH₃ H H H H H H H C-75 Ph H F H H H H H H H C-76 Ph H C₆F₅ H H H HH H H C-77 Ph H H C₆F₅ H H H H H H C-78 Ph H C₆H₅ H H H H H H H C-79 PhH H C₆H₅ H H H H H H C-80 Ph H H OCH₃ H F H F H H C-81 Ph H CF₃ H H H HF H H C-82 Ph H H ¹⁾ ¹⁾ H H H H H C-83 Ph H H H H H Si(CH₃)₂ C₆F₁₃ H H HC-84 CH₃ H H H H H H H H H C-85 Ph H C₆F₅ H H H H F H H C-86 Ph H C₆F₅ HH H H CF₃ H H C-87 Ph H C₆F₅ H H H C₆F₅ H H H C-88 Ph H C₆F₅ H H H HC₆F₅ H H C-89 Ph H H C₆F₅ H H C₆F₅ H H H C-90 Ph H H C₆F₅ H H H C₆F₅ H HC-91 Ph H H OCH₃ H F H F H H C-92 Ph H H OCH₃ H F CN F H H C-93 Ph H HOCH₃ H CF₃ H CF₃ H H C-94 Ph H H N(CH₃)₂ H F H F H H C-95 Ph H H N(CH₃)₂H F CN F H H C-96 Ph H H N(CH₃)₂ H CF₃ H CF₃ H H C-97 Ph ¹⁾ ¹⁾ H H H H HH H C-98 Ph ¹⁾ ¹⁾ H H H H CH₃ H H C-99 Ph ¹⁾ ¹⁾ H H H H OCH₃ H H C-100Ph ¹⁾ ¹⁾ H H H H N(CH₃)₂ H H C-101 Ph ¹⁾ ¹⁾ H H H CH₃ H H H C-102 Ph ¹⁾¹⁾ H H H OCH₃ H H H C-103 Ph ¹⁾ ¹⁾ H H H N(CH₃)₂ H H H C-104 Ph H H ¹⁾¹⁾ H H H H H C-105 Ph H H ¹⁾ ¹⁾ H H CH₃ H H C-106 Ph H H ¹⁾ ¹⁾ H H OCH₃H H C-107 Ph H H ¹⁾ ¹⁾ H H N(CH₃)₂ H H C-108 Ph H H ¹⁾ ¹⁾ H CH₃ H H HC-109 Ph H H ¹⁾ ¹⁾ H OCH₃ H H H C-110 Ph H H ¹⁾ ¹⁾ H N(CH₃)₂ H H H ¹⁾ Z¹= Z² = Z³ = Z⁴;

Cpd. R¹ R² R³ R⁴ R⁵ Z¹ D-1 H H H H Ph Ph D-2 H NO₂ H H Ph Ph D-3 H CH₃ HH Ph Ph D-4 H C(CH₃)₃ H H Ph Ph D-5 H CH(CH₃)₂ H H Ph Ph D-6 H CF₃ H HPh Ph D-7 H OCF₃ H H Ph Ph D-8 H F H H Ph Ph D-9 H OCH₃ H H Ph Ph D-10 HOPh H H Ph Ph D-11 H CN H H Ph Ph D-12 H SCH₃ H H Ph Ph D-13 H CO₂CH₃ HH Ph Ph D-14 H SO₂CH₃ H H Ph Ph D-15 CH₃ H H H Ph Ph D-16 F H H H Ph PhD-17 CF₃ H H H Ph Ph D-18 C(CH₃)₃ H H H Ph Ph D-19 CN H H H Ph Ph D-20NO₂ H H H Ph Ph D-21 OCH₃ H H H Ph Ph D-22 H H CH₃ H Ph Ph D-23 H H F HPh Ph D-24 H H CF₃ H Ph Ph D-25 H H OCF₃ H Ph Ph D-26 H H CN H Ph PhD-27 H H NO₂ H Ph Ph D-28 H H OCH₃ H Ph Ph D-29 H H SCH₃ H Ph Ph D-30 HC₆H₄CF₃ H H Ph Ph D-31 H H H H Ph CF₃ D-32 H NO₂ H H Ph CF₃ D-33 H CH₃ HH Ph CF₃ D-34 H C(CH₃)₃ H H Ph CF₃ D-35 H CH(CH₃)₂ H H Ph CF₃ D-36 H CF₃H H Ph CF₃ D-37 H OCF₃ H H Ph CF₃ D-38 H F H H Ph CF₃ D-39 H OCH₃ H H PhCF₃ D-40 H OPh H H Ph CF₃ D-41 H CN H H Ph CF₃ D-42 H SCH₃ H H Ph CF₃D-43 H CO₂CH₃ H H Ph CF₃ D-44 H SO₂CH₃ H H Ph CF₃ D-45 CH3 H H H Ph CF₃D-46 F H H H Ph CF₃ D-47 CF3 H H H Ph CF₃ D-48 C(CH3)3 H H H Ph CF₃ D-49CN H H H Ph CF₃ D-50 NO2 H H H Ph CF₃ D-51 OCH3 H H H Ph CF₃ D-52 H HCH₃ H Ph CF₃ D-53 H H F H Ph CF₃ D-54 H H CF₃ H Ph CF₃ D-55 H H OCF₃ HPh CF₃ D-56 H H CN H Ph CF₃ D-57 H H NO₂ H Ph CF₃ D-58 H H OCH₃ H Ph CF₃D-59 H H SCH₃ H Ph CF₃ D-60 H C₆H₄CF₃ H H Ph CF₃ D-61 H H H H Ph ¹⁾ D-62H NO₂ H H Ph ¹⁾ D-63 H CH₃ H H Ph ¹⁾ D-64 H C(CH₃)₃ H H Ph ¹⁾ D-65 HCH(CH₃)₂ H H Ph ¹⁾ D-66 H CF₃ H H Ph ¹⁾ D-67 H OCF₃ H H Ph ¹⁾ D-68 H F HH Ph ¹⁾ D-69 H OCH₃ H H Ph ¹⁾ D-70 H OPh H H Ph ¹⁾ D-71 H CN H H Ph ¹⁾D-72 H SCH₃ H H Ph ¹⁾ D-73 H CO₂CH₃ H H Ph ¹⁾ D-74 H SO₂CH₃ H H Ph ¹⁾D-75 CH3 H H H Ph ¹⁾ D-76 F H H H Ph ¹⁾ D-77 CF3 H H H Ph ¹⁾ D-78C(CH3)3 H H H Ph ¹⁾ D-79 CN H H H Ph ¹⁾ D-80 NO2 H H H Ph ¹⁾ D-81 OCH3 HH H Ph ¹⁾ D-82 H H CH₃ H Ph ¹⁾ D-83 H H F H Ph ¹⁾ D-84 H H CF₃ H Ph ¹⁾D-85 H H OCF₃ H Ph ¹⁾ D-86 H H CN H Ph ¹⁾ D-87 H H NO₂ H Ph ¹⁾ D-88 H HOCH₃ H Ph ¹⁾ D-89 H H SCH₃ H Ph ¹⁾ D-90 H C₆H₄CF₃ H H Ph ¹⁾ ¹⁾4-C₆H₄C(CH)₃;

Cpd. R¹ R² R³ R⁴ R⁵ Z¹ E-1 H H H H Ph Ph E-2 H NO₂ H H Ph Ph E-3 H CH₃ HH Ph Ph E-4 H C(CH₃)₃ H H Ph Ph E-5 H CH(CH₃)₂ H H Ph Ph E-6 H CF₃ H HPh Ph E-7 H OCF₃ H H Ph Ph E-8 H F H H Ph Ph E-9 H OCH₃ H H Ph Ph E-10 HOPh H H Ph Ph E-11 H CN H H Ph Ph E-12 H SCH₃ H H Ph Ph E-13 H CO₂CH₃ HH Ph Ph E-14 H SO₂CH₃ H H Ph Ph E-15 H C₆H₄CF₃ H H Ph Ph E-16 CH₃ H H HPh Ph E-17 F H H H Ph Ph E-18 CF₃ H H H Ph Ph E-19 C(CH₃)₃ H H H Ph PhE-20 CN H H H Ph Ph E-21 NO₂ H H H Ph Ph E-22 OCH₃ H H H Ph Ph E-23 H HCH₃ H Ph Ph E-24 H H F H Ph Ph E-25 H H CF₃ H Ph Ph E-26 H H OCF₃ H PhPh E-27 H H CN H Ph Ph E-28 H H NO₂ H Ph Ph E-29 H H OCH₃ H Ph Ph E-30 HH SCH₃ H Ph Ph E-31 H H H H Ph CF₃ E-32 H NO₂ H H Ph CF₃ E-33 H CH₃ H HPh CF₃ E-34 H C(CH₃)₃ H H Ph CF₃ E-35 H CH(CH₃)₂ H H Ph CF₃ E-36 H CF₃ HH Ph CF₃ E-37 H OCF₃ H H Ph CF₃ E-38 H F H H Ph CF₃ E-39 H OCH₃ H H PhCF₃ E-40 H OPh H H Ph CF₃ E-41 H CN H H Ph CF₃ E-42 H SCH₃ H H Ph CF₃E-43 H CO₂CH₃ H H Ph CF₃ E-44 H SO₂CH₃ H H Ph CF₃ E-45 CH₃ H H H Ph CF₃E-46 F H H H Ph CF₃ E-47 CF₃ H H H Ph CF₃ E-48 C(CH₃)₃ H H H Ph CF₃ E-49CN H H H Ph CF₃ E-50 NO₂ H H H Ph CF₃ E-51 OCH₃ H H H Ph CF₃ E-52 H HCH₃ H Ph CF₃ E-53 H H F H Ph CF₃ E-54 H H CF₃ H Ph CF₃ E-55 H H OCF₃ HPh CF₃ E-56 H H CN H Ph CF₃ E-57 H H NO₂ H Ph CF₃ E-58 H H OCH₃ H Ph CF₃E-59 H H SCH₃ H Ph CF₃ E-60 H C₆H₄CF₃ H H Ph CF₃ E-61 H H H H Ph ¹⁾ E-62H NO₂ H H Ph ¹⁾ E-63 H CH₃ H H Ph ¹⁾ E-64 H C(CH₃)₃ H H Ph ¹⁾ E-65 HCH(CH₃)₂ H H Ph ¹⁾ E-66 H CF₃ H H Ph ¹⁾ E-67 H OCF₃ H H Ph ¹⁾ E-68 H F HH Ph ¹⁾ E-69 H OCH₃ H H Ph ¹⁾ E-70 H OPh H H Ph ¹⁾ E-71 H CN H H Ph ¹⁾E-72 H SCH₃ H H Ph ¹⁾ E-73 H CO₂CH₃ H H Ph ¹⁾ E-74 H SO₂CH₃ H H Ph ¹⁾E-75 CH₃ H H H Ph ¹⁾ E-76 F H H H Ph ¹⁾ E-77 CF₃ H H H Ph ¹⁾ E-78C(CH₃)₃ H H H Ph ¹⁾ E-79 CN H H H Ph ¹⁾ E-80 NO₂ H H H Ph ¹⁾ E-81 OCH₃ HH H Ph ¹⁾ E-82 H H CH₃ H Ph ¹⁾ E-83 H H F H Ph ¹⁾ E-84 H H CF₃ H Ph ¹⁾E-85 H H OCF₃ H Ph ¹⁾ E-86 H H CN H Ph ¹⁾ E-87 H H NO₂ H Ph ¹⁾ E-88 H HOCH₃ H Ph ¹⁾ E-89 H H SCH₃ H Ph ¹⁾ E-90 H C₆H₄CF₃ H H Ph ¹⁾ ¹⁾4-C₆H₄C(CH)₃;

Cpd. R¹ R² R³ R⁴ R⁵ Z¹ = Z² F-1 H H H H Ph H F-2 H NO₂ H H Ph H F-3 HCH₃ H H Ph H F-4 H C(CH₃)₃ H H Ph H F-5 H CH(CH₃)₂ H H Ph H F-6 H CF₃ HH Ph H F-7 H OCF₃ H H Ph H F-8 H F H H Ph H F-9 H OCH₃ H H Ph H F-10 HOPh H H Ph H F-11 H CN H H Ph H F-12 H SCH₃ H H Ph H F-13 H CO₂CH₃ H HPh H F-14 H SO₂CH₃ H H Ph H F-15 CH₃ H H H Ph H F-16 F H H H Ph H F-17CF₃ H H H Ph H F-18 C(CH₃)₃ H H H Ph H F-19 CN H H H Ph H F-20 NO₂ H H HPh H F-21 OCH₃ H H H Ph H F-22 H H CH₃ H Ph H F-23 H H F H Ph H F-24 H HCF₃ H Ph H F-25 H H OCF₃ H Ph H F-26 H H CN H Ph H F-27 H H NO₂ H Ph HF-28 H H OCH₃ H Ph H F-29 H H SCH₃ H Ph H F-30 H C₆H₄CF₃ H H Ph H

Cpd. R¹ R² R³ R⁴ R⁵ ¹⁾ G-1 H H H H Ph H G-2 H NO₂ H H Ph H G-3 H CH₃ H HPh H G-4 H C(CH₃)₃ H H Ph H G-5 H CH(CH₃)₂ H H Ph H G-6 H CF₃ H H Ph HG-7 H OCF₃ H H Ph H G-8 H F H H Ph H G-9 H OCH₃ H H Ph H G-10 H OPh H HPh H G-11 H CN H H Ph H G-12 H SCH₃ H H Ph H G-13 H CO₂CH₃ H H Ph H G-14H SO₂CH₃ H H Ph H G-15 CH₃ H H H Ph H G-16 F H H H Ph H G-17 CF₃ H H HPh H G-18 C(CH₃)₃ H H H Ph H G-19 CN H H H Ph H G-20 NO₂ H H H Ph H G-21OCH₃ H H H Ph H G-22 H H CH₃ H Ph H G-23 H H F H Ph H G-24 H H CF₃ H PhH G-25 H H OCF₃ H Ph H G-26 H H CN H Ph H G-27 H H NO₂ H Ph H G-28 H HOCH₃ H Ph H G-29 H H SCH₃ H Ph H G-30 H C₆H₄CF₃ H H Ph H ¹⁾ Z¹ = Z² = Z³= Z⁴.

Cpd. R⁵ R⁶ R⁷ R⁸ R⁹ A¹⁰ A¹¹ A¹² A¹³ Z¹ H-1 Ph H H H H H H H H Ph H-2 PhH H H H H H CH₃ H Ph H-3 Ph H H H H H H Ph H Ph H-4 Ph H H H H H H t-BuH Ph H-5 Ph H H H H H H C₆H₁₁ H Ph H-6 Ph H H H H H H F H Ph H-7 Ph H HH H H H OCH₃ H Ph H-8 Ph H H H H H H OC₆H₅ H Ph H-9 Ph H H H H H H OH HPh H-10 Ph H H H H H H OCF₃ H Ph H-11 Ph H H H H H H OSi(CH₃)₂C(CH₃)₃ HPh H-12 Ph H H H H H H CF₃ H Ph H-13 Ph H H H H H H SCH₃ H Ph H-14 Ph HH H H H H SO₂CH₃ H Ph H-15 Ph H H H H H H SOCH₃ H Ph H-16 Ph H H H H H HSH H Ph H-17 Ph H H H H H H NO₂ H Ph H-18 Ph H H H H H H N(CH₃)₂ H PhH-19 Ph H H H H H H NH₂ H Ph H-20 Ph H H H H H H NCOCH₃ H Ph H-21 Ph H HH H H H NSO₂CH₃ H Ph H-22 Ph H H H H H H HNCH₂CH₃ H Ph H-23 Ph H H H H HH CHO H Ph H-24 Ph H H H H H H CH₂OH H Ph H-25 Ph H H H H H H CH₂Br H PhH-26 Ph H H H H H H CH₂CN H Ph H-27 Ph H H H H H H CH₂CO₂H H Ph H-28 PhH H H H H H CH₂OCH₃ H Ph H-29 Ph H H H H H H CH₂N(CH₂CH₃)₂ H Ph H-30 PhH H H H H H CHCHCO₂CH₃ H Ph H-31 Ph H H H H H H CH₂CH₂CO₂CH₃ H Ph H-32Ph H H H H H H C₆F₅ H Ph H-33 Ph H H H H H H H CH₃ Ph H-34 Ph H H H H HCH₃ H H Ph H-35 Ph H H H H H H H CHCH₂ Ph H-36 Ph H H H H H CHCH₂ H H PhH-37 Ph H H H H H H H Ph Ph H-38 Ph H H H H H Ph H H Ph H-39 Ph H H H HH C₆F₅ H H Ph H-40 Ph H H H H H CF₃ H CF₃ Ph H-41 Ph H H H H H H H CF₃Ph H-42 Ph H H H H H CF₃ H H Ph H-43 Ph H H H H H F H H Ph H-44 Ph H H HH H H H F Ph H-45 Ph H H H H H F H F Ph H-46 Ph H H H H H H H OCF₃ PhH-47 Ph H H H H H OCF₃ H H Ph H-48 Ph H H H H H NO₂ H CF₃ Ph H-49 Ph H HH H H CF₃ H NO₂ Ph H-50 Ph H H H H H CN H H Ph H-51 Ph H H H H H H H CNPh H-52 Ph H H H H H H H Si(CH₃)₃ Ph H-53 Ph H H H H H Si(CH₃)₃ H H PhH-54 Ph H H H H H NO₂ H CN Ph H-55 Ph H H H H H CN H NO₂ Ph H-56 Ph CF₃H H H H H H H Ph H-57 Ph Cl H H H H H H H Ph H-58 Ph NO₂ H H H H H H HPh H-59 Ph CN H H H H H H H Ph H-60 Ph CH₃ H H H H H H H Ph H-61 Ph OCH₃H H H H H H H Ph H-62 Ph Ph H H H H H H H Ph H-63 Ph F H H H H H H H PhH-64 Ph H H H CF₃ H H H H Ph H-65 Ph H H H CN H H H H Ph H-66 Ph H H HNO₂ H H H H Ph H-67 Ph H H H CH₃ H H H H Ph H-68 Ph H H H Ph H H H H PhH-69 Ph H H H F H H H H Ph H-70 Ph H H H OCH₃ H H H H Ph H-71 Ph H H CF₃H H H H H Ph H-72 Ph H H CH₃ H H H H H Ph H-73 Ph H CF₃ H H H H H H PhH-74 Ph H CH₃ H H H H H H Ph H-75 Ph H F H H H H H H Ph H-76 Ph H C₆F₅ HH H H H H Ph H-77 Ph H H C₆F₅ H H H H H Ph H-78 Ph H C₆H₅ H H H H H H PhH-79 Ph H H C₆H₅ H H H H H Ph H-80 Ph H CF₃ H H H H F H Ph H-81 Ph H F HH H H CF₃ H Ph H-82 Ph H CN H H H H F H Ph H-83 Ph H H H H HSi(CH₃)₂C₆F₁₃ H H Ph H-84 Ph H F H H H F CN H Ph H-85 Ph H C₆F₅ H H H HF H Ph H-86 Ph H C₆F₅ H H H H CF₃ H Ph H-87 Ph H C₆F₅ H H H C₆F₅ H H PhH-88 Ph H C₆F₅ H H H H C₆F₅ H Ph H-89 Ph H H C₆F₅ H H C₆F₅ H H Ph H-90Ph H H C₆F₅ H H H C₆F₅ H Ph H-91 Ph H H OCH₃ H F H F H Ph H-92 Ph H HOCH₃ H F CN F H Ph H-93 Ph H H OCH₃ H CF₃ H CF₃ H Ph H-94 Ph H H N(CH₃)₂H F H F H PH H-95 Ph H H N(CH₃)₂ H F CN F H Ph H-96 Ph H H N(CH₃)₂ H CF₃H CF₃ H Ph H-97 Ph ¹⁾ ¹⁾ H H H H H H Ph H-98 Ph ¹⁾ ¹⁾ H H H H CH₃ H PhH-99 Ph ¹⁾ ¹⁾ H H H H OCH₃ H Ph H-100 Ph ¹⁾ ¹⁾ H H H H N(CH₃)₂ H PhH-101 Ph ¹⁾ ¹⁾ H H H CH₃ H H Ph H-102 Ph ¹⁾ ¹⁾ H H H OCH₃ H H Ph H-103Ph ¹⁾ ¹⁾ H H H N(CH₃)₂ H H Ph H-104 Ph H H ¹⁾ ¹⁾ H H H H Ph H-105 Ph H H¹⁾ ¹⁾ H H CH₃ H Ph H-106 Ph H H ¹⁾ ¹⁾ H H OCH₃ H Ph H-107 Ph H H ¹⁾ ¹⁾ HH N(CH₃)₂ H Ph H-108 Ph H H ¹⁾ ¹⁾ H CH₃ H H Ph H-109 Ph H H ¹⁾ ¹⁾ H OCH₃H H Ph H-110 Ph H H ¹⁾ ¹⁾ H N(CH₃)₂ H H Ph H-111 Ph H H H H H H H H CF₃H-112 Ph H H H H H H CH₃ H CF₃ H-113 Ph H H H H H H Ph H CF₃ H-114 Ph HH H H H H t-Bu H CF₃ H-115 Ph H H H H H H C₆H₁₁ H CF₃ H-116 Ph H H H H HH F H CF₃ H-117 Ph H H H H H H OCH₃ H CF₃ H-118 Ph H H H H H H OC₆H₅ HCF₃ H-119 Ph H H H H H H OH H CF₃ H-120 Ph H H H H H H OCF₃ H CF₃ H-121Ph H H H H H H OSi(CH₃)₂C(CH₃)₃ H CF₃ H-122 Ph H H H H H H CF₃ H CF₃H-123 Ph H H H H H H SCH₃ H CF₃ H-124 Ph H H H H H H SO₂CH₃ H CF₃ H-125Ph H H H H H H SOCH₃ H CF₃ H-126 Ph H H H H H H SH H CF₃ H-127 Ph H H HH H H NO₂ H CF₃ H-128 Ph H H H H H H N(CH₃)₂ H CF₃ H-129 Ph H H H H H HNH₂ H CF₃ H-130 Ph H H H H H H NCOCH₃ H CF₃ H-131 Ph H H H H H H NSO₂CH₃H CF₃ H-132 Ph H H H H H H HNCH₂CH₃ H CF₃ H-133 Ph H H H H H H CHO H CF₃H-134 Ph H H H H H H CH₂OH H CF₃ H-135 Ph H H H H H H CH₂Br H CF₃ H-136Ph H H H H H H CH₂CN H CF₃ H-137 Ph H H H H H H CH₂CO₂H H CF₃ H-138 Ph HH H H H H CH₂OCH₃ H CF₃ H-139 Ph H H H H H H CH₂N(CH₂CH₃)₂ H CF₃ H-140Ph H H H H H H CHCHCO₂CH₃ H CF₃ H-141 Ph H H H H H H CH₂CH₂CO₂CH₃ H CF₃H-142 Ph H H H H H H C₆F₅ H CF₃ H-143 Ph H H H H H H H CH₃ CF₃ H-144 PhH H H H H CH₃ H H CF₃ H-145 Ph H H H H H H H CHCH₂ CF₃ H-146 Ph H H H HH CHCH₂ H H CF₃ H-147 Ph H H H H H H H Ph CF₃ H-148 Ph H H H H H Ph H HCF₃ H-149 Ph H H H H H C₆F₅ H H CF₃ H-150 Ph H H H H H CF₃ H CF₃ CF₃H-151 Ph H H H H H H H CF₃ CF₃ H-152 Ph H H H H H CF₃ H H CF₃ H-153 Ph HH H H H F H H CF₃ H-154 Ph H H H H H H H F CF₃ H-155 Ph H H H H H F H FCF₃ H-156 Ph H H H H H H H OCF₃ CF₃ H-157 Ph H H H H H OCF₃ H H CF₃H-158 Ph H H H H H NO₂ H CF₃ CF₃ H-159 Ph H H H H H CF₃ H NO₂ CF₃ H-160Ph H H H H H CN H H CF₃ H-161 Ph H H H H H H H CN CF₃ H-152 Ph H H H H HH H Si(CH₃)₃ CF₃ H-163 Ph H H H H H Si(CH₃)₃ H H CF₃ H-164 Ph H H H H HNO₂ H CN CF₃ H-165 Ph H H H H H CN H NO₂ CF₃ H-166 Ph CF₃ H H H H H H HCF₃ H-167 Ph Cl H H H H H H H CF₃ H-168 Ph NO₂ H H H H H H H CF₃ H-169Ph CN H H H H H H H CF₃ H-170 Ph CH₃ H H H H H H H CF₃ H-171 Ph OCH₃ H HH H H H H CF₃ H-172 Ph Ph H H H H H H H CF₃ H-173 Ph F H H H H H H H CF₃H-174 Ph H H H CF₃ H H H H CF₃ H-175 Ph H H H CN H H H H CF₃ H-176 Ph HH H NO₂ H H H H CF₃ H-177 Ph H H H CH₃ H H H H CF₃ H-178 Ph H H H Ph H HH H CF₃ H-179 Ph H H H F H H H H CF₃ H-180 Ph H H H OCH₃ H H H H CF₃H-181 Ph H H CF₃ H H H H H CF₃ H-182 Ph H H CH₃ H H H H H CF₃ H-183 Ph HCF₃ H H H H H H CF₃ H-184 Ph H CH₃ H H H H H H CF₃ H-185 Ph H F H H H HH H CF₃ H-186 Ph H C₆F₅ H H H H H H CF₃ H-187 Ph H H C₆F₅ H H H H H CF₃H-188 Ph H C₆H₅ H H H H H H CF₃ H-189 Ph H H C₆H₅ H H H H H CF₃ H-190 PhH CF₃ H H H H F H CF₃ H-191 Ph H F H H H H CF₃ H CF₃ H-192 Ph H CN H H HH F H CF₃ H-193 Ph H H H H H Si(CH₃)₂C₆F₁₃ H H CF₃ H-194 Ph H F H H H FCN H CF₃ H-195 Ph H C₆F₅ H H H H F H CF₃ H-196 Ph H C₆F₅ H H H H CF₃ HCF₃ H-197 Ph H C₆F₅ H H H C₆F₅ H H CF₃ H-198 Ph H C₆F₅ H H H H C₆F₅ HCF₃ H-199 Ph H H C₆F₅ H H C₆F₅ H H CF₃ H-200 Ph H H C₆F₅ H H H C₆F₅ HCF₃ H-201 Ph H H OCH₃ H F H F H CF₃ H-202 Ph H H OCH₃ H F CN F H CF₃H-203 Ph H H OCH₃ H CF₃ H CF₃ H CF₃ H-204 Ph H H N(CH₃)₂ H F H F H CF₃H-205 Ph H H N(CH₃)₂ H F CN F H CF₃ H-206 Ph H H N(CH₃)₂ H CF₃ H CF₃ HCF₃ H-207 Ph ¹⁾ ¹⁾ H H H H H H CF₃ H-208 Ph ¹⁾ ¹⁾ H H H H CH₃ H CF₃H-209 Ph ¹⁾ ¹⁾ H H H H OCH₃ H CF₃ H-210 Ph ¹⁾ ¹⁾ H H H H N(CH₃)₂ H CF₃H-211 Ph ¹⁾ ¹⁾ H H H CH₃ H H CF₃ H-212 Ph ¹⁾ ¹⁾ H H H OCH₃ H H CF₃ H-213Ph ¹⁾ ¹⁾ H H H N(CH₃)₂ H H CF₃ H-214 Ph H H ¹⁾ ¹⁾ H H H H CF₃ H-215 Ph HH ¹⁾ ¹⁾ H H CH₃ H CF₃ H-216 Ph H H ¹⁾ ¹⁾ H H OCH₃ H CF₃ H-217 Ph H H ¹⁾¹⁾ H H N(CH₃)₂ H CF₃ H-218 Ph H H ¹⁾ ¹⁾ H CH₃ H H CF₃ H-219 Ph H H ¹⁾ ¹⁾H OCH₃ H H CF₃ H-210 Ph H H ¹⁾ ¹⁾ H N(CH₃)₂ H H CF₃ H-211 Ph H H H H H HH H ²⁾ H-212 Ph H H H H H H CH₃ H ²⁾ H-213 Ph H H H H H H Ph H ²⁾ H-214Ph H H H H H H t-Bu H ²⁾ H-215 Ph H H H H H H C₆H₁₁ H ²⁾ H-216 Ph H H HH H H F H ²⁾ H-217 Ph H H H H H H OCH₃ H ²⁾ H-218 Ph H H H H H H OC₆H₅ H²⁾ H-219 Ph H H H H H H OH H ²⁾ H-220 Ph H H H H H H OCF₃ H ²⁾ H-221 PhH H H H H H OSi(CH₃)₂C(CH₃)₃ H ²⁾ H-222 Ph H H H H H H CF₃ H ²⁾ H-223 PhH H H H H H SCH₃ H ²⁾ H-224 Ph H H H H H H SO₂CH₃ H ²⁾ H-225 Ph H H H HH H SOCH₃ H ²⁾ H-226 Ph H H H H H H SH H ²⁾ H-227 Ph H H H H H H NO₂ H²⁾ H-228 Ph H H H H H H N(CH₃)₂ H ²⁾ H-229 Ph H H H H H H NH₂ H ²⁾ H-230Ph H H H H H H NCOCH₃ H ²⁾ H-231 Ph H H H H H H NSO₂CH₃ H ²⁾ H-232 Ph HH H H H H HNCH₂CH₃ H ²⁾ H-233 Ph H H H H H H CHO H ²⁾ H-234 Ph H H H H HH CH₂OH H ²⁾ H-235 Ph H H H H H H CH₂Br H ²⁾ H-236 Ph H H H H H H CH₂CNH ²⁾ H-237 Ph H H H H H H CH₂CO₂H H ²⁾ H-238 Ph H H H H H H CH₂OCH₃ H ²⁾H-239 Ph H H H H H H CH₂N(CH₂CH₃)₂ H ²⁾ H-240 Ph H H H H H H CHCHCO₂CH₃H ²⁾ H-241 Ph H H H H H H CH₂CH₂CO₂CH₃ H ²⁾ H-242 Ph H H H H H H C₆F₅ H²⁾ H-243 Ph H H H H H H H CH₃ ²⁾ H-244 Ph H H H H H CH₃ H H ²⁾ H-245 PhH H H H H H H CHCH₂ ²⁾ H-246 Ph H H H H H CHCH₂ H H ²⁾ H-247 Ph H H H HH H H Ph ²⁾ H-248 Ph H H H H H Ph H H ²⁾ H-249 Ph H H H H H C₆F₅ H H ²⁾H-250 Ph H H H H H CF₃ H CF₃ ²⁾ H-251 Ph H H H H H H H CF₃ ²⁾ H-252 Ph HH H H H CF₃ H H ²⁾ H-253 Ph H H H H H F H H ²⁾ H-254 Ph H H H H H H H F²⁾ H-255 Ph H H H H H F H F ²⁾ H-256 Ph H H H H H H H OCF₃ ²⁾ H-257 Ph HH H H H OCF₃ H H ²⁾ H-258 Ph H H H H H NO₂ H CF₃ ²⁾ H-259 Ph H H H H HCF₃ H NO₂ ²⁾ H-260 Ph H H H H H CN H H ²⁾ H-261 Ph H H H H H H H CN ²⁾H-252 Ph H H H H H H H Si(CH₃)₃ ²⁾ H-263 Ph H H H H H Si(CH₃)₃ H H ²⁾H-264 Ph H H H H H NO₂ H CN ²⁾ H-265 Ph H H H H H CN H NO₂ ²⁾ H-266 PhCF₃ H H H H H H H ²⁾ H-267 Ph Cl H H H H H H H ²⁾ H-268 Ph NO₂ H H H H HH H ²⁾ H-269 Ph CN H H H H H H H ²⁾ H-270 Ph CH₃ H H H H H H H ²⁾ H-271Ph OCH₃ H H H H H H H ²⁾ H-272 Ph Ph H H H H H H H ²⁾ H-273 Ph F H H H HH H H ²⁾ H-274 Ph H H H CF₃ H H H H ²⁾ H-275 Ph H H H CN H H H H ²⁾H-276 Ph H H H NO₂ H H H H ²⁾ H-277 Ph H H H CH₃ H H H H ²⁾ H-278 Ph H HH Ph H H H H ²⁾ H-279 Ph H H H F H H H H ²⁾ H-280 Ph H H H OCH₃ H H H H²⁾ H-281 Ph H H CF₃ H H H H H ²⁾ H-282 Ph H H CH₃ H H H H H ²⁾ H-283 PhH CF₃ H H H H H H ²⁾ H-284 Ph H CH₃ H H H H H H ²⁾ H-285 Ph H F H H H HH H ²⁾ H-286 Ph H C₆F₅ H H H H H H ²⁾ H-287 Ph H H C₆F₅ H H H H H ²⁾H-288 Ph H C₆H₅ H H H H H H ²⁾ H-289 Ph H H C₆H₅ H H H H H ²⁾ H-290 Ph HCF₃ H H H H F H ²⁾ H-291 Ph H F H H H H CF₃ H ²⁾ H-292 Ph H CN H H H H FH ²⁾ H-293 Ph H H H H H Si(CH₃)₂C₆F₅ H H ²⁾ H-294 Ph H F H H H F CN H ²⁾H-295 Ph H C₆F₅ H H H H F H ²⁾ H-296 Ph H C₆F₅ H H H H CF₃ H ²⁾ H-297 PhH C₆F₅ H H H C₆F₅ H H ²⁾ H-298 Ph H C₆F₅ H H H H C₆F₅ H ²⁾ H-299 Ph H HC₆F₅ H H C₆F₅ H H ²⁾ H-300 Ph H H C₆F₅ H H H C₆F₅ H ²⁾ H-301 Ph H H OCH₃H F H F H ²⁾ H-302 Ph H H OCH₃ H F CN F H ²⁾ H-303 Ph H H OCH₃ H CF₃ HCF₃ H ²⁾ H-304 Ph H H N(CH₃)₂ H F H F H ²⁾ H-305 Ph H H- N(CH₃)₂ H F CNF H ²⁾ H-306 Ph H H N(CH₃)₂ H CF₃ H CF₃ H ²⁾ H-307 Ph ¹⁾ ¹⁾ H H H H H H²⁾ H-308 Ph ¹⁾ ¹⁾ H H H H CH₃ H ²⁾ H-309 Ph ¹⁾ ¹⁾ H H H H OCH₃ H ²⁾H-310 Ph ¹⁾ ¹⁾ H H H H N(CH₃)₂ H ²⁾ H-311 Ph ¹⁾ ¹⁾ H H H CH₃ H H ²⁾H-312 Ph ¹⁾ ¹⁾ H H H OCH₃ H H ²⁾ H-313 Ph ¹⁾ ¹⁾ H H H N(CH₃)₂ H H ²⁾H-314 Ph H H ¹⁾ ¹⁾ H H H H ²⁾ H-315 Ph H H ¹⁾ ¹⁾ H H CH₃ H ²⁾ H-316 Ph HH ¹⁾ ¹⁾ H H OCH₃ H ²⁾ H-317 Ph H H ¹⁾ ¹⁾ H H N(CH₃)₂ H ²⁾ H-318 Ph H H¹⁾ ¹⁾ H CH₃ H H ²⁾ H-319 Ph H H ¹⁾ ¹⁾ H OCH₃ H H ²⁾ H-320 Ph H H ¹⁾ ¹⁾ HN(CH₃)₂ H H ²⁾

²⁾ 4-C₆H₄C(CH)₃.

Cpd. R⁵ R⁶ R⁷ R⁸ R⁹ A¹⁰ A¹¹ A¹² A¹³ Z¹ H′-1 Ph H H H H H H H H Ph H′-2Ph H H H H H H CH₃ H Ph H′-3 Ph H H H H H H Ph H Ph H′-4 Ph H H H H H Ht-Bu H Ph H′-5 Ph H H H H H H C₆H₁₁ H Ph H′-6 Ph H H H H H H F H Ph H′-7Ph H H H H H H OCH₃ H Ph H′-8 Ph H H H H H H OC₆H₅ H Ph H′-9 Ph H H H HH H OH H Ph H′-10 Ph H H H H H H OCF₃ H Ph H′-11 Ph H H H H H HOSi(CH₃)₂C(CH₃)₃ H Ph H′-12 Ph H H H H H H CF₃ H Ph H′-13 Ph H H H H H HSCH₃ H Ph H′-14 Ph H H H H H H SO₂CH₃ H Ph H′-15 Ph H H H H H H SOCH₃ HPh H′-16 Ph H H H H H H SH H Ph H′-17 Ph H H H H H H NO₂ H Ph H′-18 Ph HH H H H H N(CH₃)₂ H Ph H′-19 Ph H H H H H H NH₂ H Ph H′-20 Ph H H H H HH NCOCH₃ H Ph H′-21 Ph H H H H H H NSO₂CH₃ H Ph H′-22 Ph H H H H H HHNCH₂CH₃ H Ph H′-23 Ph H H H H H H CHO H Ph H′-24 Ph H H H H H H CH₂OH HPh H′-25 Ph H H H H H H CH₂Br H Ph H′-26 Ph H H H H H H CH₂CN H Ph H′-27Ph H H H H H H CH₂CO₂H H Ph H′-28 Ph H H H H H H CH₂OCH₃ H Ph H′-29 Ph HH H H H H CH₂N(CH₂CH₃)₂ H Ph H′-30 Ph H H H H H H CHCHCO₂CH₃ H Ph H′-31Ph H H H H H H CH₂CH₂CO₂CH₃ H Ph H′-32 Ph H H H H H H C₆F₅ H Ph H′-33 PhH H H H H H H CH₃ Ph H′-34 Ph H H H H H CH₃ H H Ph H′-35 Ph H H H H H HH CHCH₂ Ph H′-36 Ph H H H H H CHCH₂ H H Ph H′-37 Ph H H H H H H H Ph PhH′-38 Ph H H H H H Ph H H Ph H′-39 Ph H H H H H C₆F₅ H H Ph H′-40 Ph H HH H H CF₃ H CF₃ Ph H′-41 Ph H H H H H H H CF₃ Ph H′-42 Ph H H H H H CF₃H H Ph H′-43 Ph H H H H H F H H Ph H′-44 Ph H H H H H H H F Ph H′-45 PhH H H H H F H F Ph H′-46 Ph H H H H H H H OCF₃ Ph H′-47 Ph H H H H HOCF₃ H H Ph H′-48 Ph H H H H H NO₂ H CF₃ Ph H′-49 Ph H H H H H CF₃ H NO₂Ph H′-50 Ph H H H H H CN H H Ph H′-51 Ph H H H H H H H CN Ph H′-52 Ph HH H H H H H Si(CH₃)₃ Ph H′-53 Ph H H H H H Si(CH₃)₃ H H Ph H′-54 Ph H HH H H NO₂ H CN Ph H′-55 Ph H H H H H CN H NO₂ Ph H′-56 Ph CF₃ H H H H HH H Ph H′-57 Ph Cl H H H H H H H Ph H′-58 Ph NO₂ H H H H H H H Ph H′-59Ph CN H H H H H H H Ph H′-60 Ph CH₃ H H H H H H H Ph H′-61 Ph OCH₃ H H HH H H H Ph H′-62 Ph Ph H H H H H H H Ph H′-63 Ph F H H H H H H H PhH′-64 Ph H H H CF₃ H H H H Ph H′-65 Ph H H H CN H H H H Ph H′-66 Ph H HH NO₂ H H H H Ph H′-67 Ph H H H CH₃ H H H H Ph H′-68 Ph H H H Ph H H H HPh H′-69 Ph H H H F H H H H Ph H′-70 Ph H H H OCH₃ H H H H Ph H′-71 Ph HH CF₃ H H H H H Ph H′-72 Ph H H CH₃ H H H H H Ph H′-73 Ph H CF₃ H H H HH H Ph H′-74 Ph H CH₃ H H H H H H Ph H′-75 Ph H F H H H H H H Ph H′-76Ph H C₆F₅ H H H H H H Ph H′-77 Ph H H C₆F₅ H H H H H Ph H′-78 Ph H C₆H₅H H H H H H Ph H′-79 Ph H H C₆H₅ H H H H H Ph H′-80 Ph H CF₃ H H H H F HPh H′-81 Ph H F H H H H CF₃ H Ph H′-82 Ph H CN H H H H F H Ph H′-83 Ph HH H H H Si(CH₃)₂C₆F₁₃ H H Ph H′-84 Ph H F H H H F CN H Ph H′-85 Ph HC₆F₅ H H H H F H Ph H′-86 Ph H C₆F₅ H H H H CF₃ H Ph H′-87 Ph H C₆F₅ H HH C₆F₅ H H Ph H′-88 Ph H C₆F₅ H H H H C₆F₅ H Ph H′-89 Ph H H C₆F₅ H HC₆F₅ H H Ph H′-90 Ph H H C₆F₅ H H H C₆F₅ H Ph H′-91 Ph H H OCH₃ H F H FH Ph H′-92 Ph H H OCH₃ H F CN F H Ph H′-93 Ph H H OCH₃ H CF₃ H CF₃ H PhH′-94 Ph H H N(CH₃)₂ H F H F H PH H′-95 Ph H H N(CH₃)₂ H F CN F H PhH′-96 Ph H H N(CH₃)₂ H CF₃ H CF₃ H Ph H′-97 Ph ¹⁾ ¹⁾ H H H H H H PhH′-98 Ph ¹⁾ ¹⁾ H H H H CH₃ H Ph H′-99 Ph ¹⁾ ¹⁾ H H H H OCH₃ H Ph H′-100Ph ¹⁾ ¹⁾ H H H H N(CH₃)₂ H Ph H′-101 Ph ¹⁾ ¹⁾ H H H CH₃ H H Ph H′-102 Ph¹⁾ ¹⁾ H H H OCH₃ H H Ph H′-103 Ph ¹⁾ ¹⁾ H H H N(CH₃)₂ H H Ph H′-104 Ph HH ¹⁾ ¹⁾ H H H H Ph H′-105 Ph H H ¹⁾ ¹⁾ H H CH₃ H Ph H′-106 Ph H H ¹⁾ ¹⁾H H OCH₃ H Ph H′-107 Ph H H ¹⁾ ¹⁾ H H N(CH₃)₂ H Ph H′-108 Ph H H ¹⁾ ¹⁾ HCH₃ H H Ph H′-109 Ph H H ¹⁾ ¹⁾ H OCH₃ H H Ph H′-110 Ph H H ¹⁾ ¹⁾ HN(CH₃)₂ H H Ph H′-111 Ph H H H H H H H H CF₃ H′-112 Ph H H H H H H CH₃ HCF₃ H′-113 Ph H H H H H H Ph H CF₃ H′-114 Ph H H H H H H t-Bu H CF₃H′-115 Ph H H H H H H C₆H₁₁ H CF₃ H′-116 Ph H H H H H H F H CF₃ H′-117Ph H H H H H H OCH₃ H CF₃ H′-118 Ph H H H H H H OC₆H₅ H CF₃ H′-119 Ph HH H H H H OH H CF₃ H′-120 Ph H H H H H H OCF₃ H CF₃ H′-121 Ph H H H H HH OSi(CH₃)₂C(CH₃)₃ H CF₃ H′-122 Ph H H H H H H CF₃ H CF₃ H′-123 Ph H H HH H H SCH₃ H CF₃ H′-124 Ph H H H H H H SO₂CH₃ H CF₃ H′-125 Ph H H H H HH SOCH₃ H CF₃ H′-126 Ph H H H H H H SH H CF₃ H′-127 Ph H H H H H H NO₂ HCF₃ H′-128 Ph H H H H H H N(CH₃)₂ H CF₃ H′-129 Ph H H H H H H NH₂ H CF₃H′-130 Ph H H H H H H NCOCH₃ H CF₃ H′-131 Ph H H H H H H NSO₂CH₃ H CF₃H′-132 Ph H H H H H H HNCH₂CH₃ H CF₃ H′-133 Ph H H H H H H CHO H CF₃H′-134 Ph H H H H H H CH₂OH H CF₃ H′-135 Ph H H H H H H CH₂Br H CF₃H′-136 Ph H H H H H H CH₂CN H CF₃ H′-137 Ph H H H H H H CH₂CO₂H H CF₃H′-138 Ph H H H H H H CH₂OCH₃ H CF₃ H′-139 Ph H H H H H H CH₂N(CH₂CH₃)₂H CF₃ H′-140 Ph H H H H H H CHCHCO₂CH₃ H CF₃ H′-141 Ph H H H H H HCH₂CH₂CO₂CH₃ H CF₃ H′-142 Ph H H H H H H C₆F₅ H CF₃ H′-143 Ph H H H H HH H CH₃ CF₃ H′-144 Ph H H H H H CH₃ H H CF₃ H′-145 Ph H H H H H H HCHCH₂ CF₃ H′-146 Ph H H H H H CHCH₂ H H CF₃ H′-147 Ph H H H H H H H PhCF₃ H′-148 Ph H H H H H Ph H H CF₃ H′-149 Ph H H H H H C₆F₅ H H CF₃H′-150 Ph H H H H H CF₃ H CF₃ CF₃ H′-151 Ph H H H H H H H CF₃ CF₃ H′-152Ph H H H H H CF₃ H H CF₃ H′-153 Ph H H H H H F H H CF₃ H′-154 Ph H H H HH H H F CF₃ H′-155 Ph H H H H H F H F CF₃ H′-156 Ph H H H H H H H OCF₃CF₃ H′-157 Ph H H H H H OCF₃ H H CF₃ H′-158 Ph H H H H H NO₂ H CF₃ CF₃H′-159 Ph H H H H H CF₃ H NO₂ CF₃ H′-160 Ph H H H H H CN H H CF₃ H′-161Ph H H H H H H H CN CF₃ H′-162 Ph H H H H H H H Si(CH₃)₃ CF₃ H′-163 Ph HH H H H Si(CH₃)₃ H H CF₃ H′-164 Ph H H H H H NO₂ H CN CF₃ H′-165 Ph H HH H H CN H NO₂ CF₃ H′-166 Ph CF₃ H H H H H H H CF₃ H′-167 Ph Cl H H H HH H H CF₃ H′-168 Ph NO₂ H H H H H H H CF₃ H′-169 Ph CN H H H H H H H CF₃H′-170 Ph CH₃ H H H H H H H CF₃ H′-171 Ph OCH₃ H H H H H H H CF₃ H′-172Ph Ph H H H H H H H CF₃ H′-173 Ph F H H H H H H H CF₃ H′-174 Ph H H HCF₃ H H H H CF₃ H′-175 Ph H H H CN H H H H CF₃ H′-176 Ph H H H NO₂ H H HH CF₃ H′-177 Ph H H H CH₃ H H H H CF₃ H′-178 Ph H H H Ph H H H H CF₃H′-179 Ph H H H F H H H H CF₃ H′-180 Ph H H H OCH₃ H H H H CF₃ H′-181 PhH H CF₃ H H H H H CF₃ H′-182 Ph H H CH₃ H H H H H CF₃ H′-183 Ph H CF₃ HH H H H H CF₃ H′-184 Ph H CH₃ H H H H H H CF₃ H′-185 Ph H F H H H H H HCF₃ H′-186 Ph H C₆F₅ H H H H H H CF₃ H′-187 Ph H H C₆F₅ H H H H H CF₃H′-188 Ph H C₆H₅ H H H H H H CF₃ H′-189 Ph H H C₆H₅ H H H H H CF₃ H′-190Ph H CF₃ H H H H F H CF₃ H′-191 Ph H F H H H H CF₃ H CF₃ H′-192 Ph H CNH H H H F H CF₃ H′-193 Ph H H H H H Si(CH₃)₂C₆F₁₃ H H CF₃ H′-194 Ph H FH H H F CN H CF₃ H′-195 Ph H C₆F₅ H H H H F H CF₃ H′-196 Ph H C₆F₅ H H HH CF₃ H CF₃ H′-197 Ph H C₆F₅ H H H C₆F₅ H H CF₃ H′-198 Ph H C₆F₅ H H H HC₆F₅ H CF₃ H′-199 Ph H H C₆F₅ H H C₆F₅ H H CF₃ H′-200 Ph H H C₆F₅ H H HC₆F₅ H CF₃ H′-201 Ph H H OCH₃ H F H F H CF₃ H′-202 Ph H H OCH₃ H F CN FH CF₃ H′-203 Ph H H OCH₃ H CF₃ H CF₃ H CF₃ H′-204 Ph H H N(CH₃)₂ H F H FH CF₃ H′-205 Ph H H N(CH₃)₂ H F CN F H CF₃ H′-206 Ph H H N(CH₃)₂ H CF₃ HCF₃ H CF₃ H′-207 Ph ¹⁾ ¹⁾ H H H H H H CF₃ H′-208 Ph ¹⁾ ¹⁾ H H H H CH₃ HCF₃ H′-209 Ph ¹⁾ ¹⁾ H H H H OCH₃ H CF₃ H′-210 Ph ¹⁾ ¹⁾ H H H H N(CH₃)₂ HCF₃ H′-211 Ph ¹⁾ ¹⁾ H H H CH₃ H H CF₃ H′-212 Ph ¹⁾ ¹⁾ H H H OCH₃ H H CF₃H′-213 Ph ¹⁾ ¹⁾ H H H N(CH₃)₂ H H CF₃ H′-214 Ph H H ¹⁾ ¹⁾ H H H H CF₃H′-215 Ph H H ¹⁾ ¹⁾ H H CH₃ H CF₃ H′-216 Ph H H ¹⁾ ¹⁾ H H OCH₃ H CF₃H′-217 Ph H H ¹⁾ ¹⁾ H H N(CH₃)₂ H CF₃ H′-218 Ph H H ¹⁾ ¹⁾ H CH₃ H H CF₃H′-219 Ph H H ¹⁾ ¹⁾ H OCH₃ H H CF₃ H′-220 Ph H H ¹⁾ ¹⁾ H N(CH₃)₂ H H CF₃H′-221 Ph H H H H H H H H ²⁾ H′-222 Ph H H H H H H CH₃ H ²⁾ H′-223 Ph HH H H H H Ph H ²⁾ H′-224 Ph H H H H H H t-Bu H ²⁾ H′-225 Ph H H H H H HC₆H₁₁ H ²⁾ H′-226 Ph H H H H H H F H ²⁾ H′-227 Ph H H H H H H OCH₃ H ²⁾H′-228 Ph H H H H H H OC₆H₅ H ²⁾ H′-229 Ph H H H H H H OH H ²⁾ H′-230 PhH H H H H H OCF₃ H ²⁾ H′-231 Ph H H H H H H OSi(CH₃)₂C(CH₃)₃ H ²⁾ H′-232Ph H H H H H H CF₃ H ²⁾ H′-233 Ph H H H H H H SCH₃ H ²⁾ H′-234 Ph H H HH H H SO₂CH₃ H ²⁾ H′-235 Ph H H H H H H SOCH₃ H ²⁾ H′-236 Ph H H H H H HSH H ²⁾ H′-237 Ph H H H H H H NO₂ H ²⁾ H′-238 Ph H H H H H H N(CH₃)₂ H²⁾ H′-239 Ph H H H H H H NH₂ H ²⁾ H′-240 Ph H H H H H H NCOCH₃ H ²⁾H′-241 Ph H H H H H H NSO₂CH₃ H ²⁾ H′-242 Ph H H H H H H HNCH₂CH₃ H ²⁾H′-243 Ph H H H H H H CHO H ²⁾ H′-244 Ph H H H H H H CH₂OH H ²⁾ H′-245Ph H H H H H H CH₂Br H ²⁾ H′-246 Ph H H H H H H CH₂CN H ²⁾ H′-247 Ph H HH H H H CH₂CO₂H H ²⁾ H′-248 Ph H H H H H H CH₂OCH₃ H ²⁾ H′-249 Ph H H HH H H CH₂N(CH₂CH₃)₂ H ²⁾ H′-250 Ph H H H H H H CHCHCO₂CH₃ H ²⁾ H′-251 PhH H H H H H CH₂CH₂CO₂CH₃ H ²⁾ H′-252 Ph H H H H H H C₆F₅ H ²⁾ H′-253 PhH H H H H H H CH₃ ²⁾ H′-254 Ph H H H H H CH₃ H H ²⁾ H′-255 Ph H H H H HH H CHCH₂ ²⁾ H′-256 Ph H H H H H CHCH₂ H H ²⁾ H′-257 Ph H H H H H H H Ph²⁾ H′-258 Ph H H H H H Ph H H ²⁾ H′-259 Ph H H H H H C₆F₅ H H ²⁾ H′-260Ph H H H H H CF₃ H CF₃ ²⁾ H′-261 Ph H H H H H H H CF₃ ²⁾ H′-262 Ph H H HH H CF₃ H H ²⁾ H′-263 Ph H H H H H F H H ²⁾ H′-264 Ph H H H H H H H F ²⁾H′-265 Ph H H H H H F H F ²⁾ H′-266 Ph H H H H H H H OCF₃ ²⁾ H′-267 Ph HH H H H OCF₃ H H ²⁾ H′-268 Ph H H H H H NO₂ H CF₃ ²⁾ H′-269 Ph H H H H HCF₃ H NO₂ ²⁾ H′-270 Ph H H H H H CN H H ²⁾ H′-271 Ph H H H H H H H CN ²⁾H′-272 Ph H H H H H H H Si(CH₃)₃ ²⁾ H′-273 Ph H H H H H Si(CH₃)₃ H H ²⁾H′-274 Ph H H H H H NO₂ H CN ²⁾ H′-275 Ph H H H H H CN H NO₂ ²⁾ H′-276Ph CF₃ H H H H H H H ²⁾ H′-277 Ph Cl H H H H H H H ²⁾ H′-278 Ph NO₂ H HH H H H H ²⁾ H′-279 Ph CN H H H H H H H ²⁾ H′-280 Ph CH₃ H H H H H H H²⁾ H′-281 Ph OCH₃ H H H H H H H ²⁾ H′-282 Ph Ph H H H H H H H ²⁾ H′-283Ph F H H H H H H H ²⁾ H′-284 Ph H H H CF₃ H H H H ²⁾ H′-285 Ph H H H CNH H H H ²⁾ H′-286 Ph H H H NO₂ H H H H ²⁾ H′-287 Ph H H H CH₃ H H H H ²⁾H′-288 Ph H H H Ph H H H H ²⁾ H′-289 Ph H H H F H H H H ²⁾ H′-290 Ph H HH OCH₃ H H H H ²⁾ H′-291 Ph H H CF₃ H H H H H ²⁾ H′-292 Ph H H CH₃ H H HH H ²⁾ H′-293 Ph H CF₃ H H H H H H ²⁾ H′-294 Ph H CH₃ H H H H H H ²⁾H′-295 Ph H F H H H H H H ²⁾ H′-296 Ph H C₆F₅ H H H H H H ²⁾ H′-297 Ph HH C₆F₅ H H H H H ²⁾ H′-298 Ph H C₆H₅ H H H H H H ²⁾ H′-299 Ph H H C₆H₅ HH H H H ²⁾ H′-300 Ph H CF₃ H H H H F H ²⁾ H′-301 Ph H F H H H H CF₃ H ²⁾H′-302 Ph H CN H H H H F H ²⁾ H′-303 Ph H H H H H Si(CH₃)₂C₆F₅ H H ²⁾H′-304 Ph H F H H H F CN H ²⁾ H′-305 Ph H C₆F₅ H H H H F H ²⁾ H′-306 PhH C₆F₅ H H H H CF₃ H ²⁾ H′-307 Ph H C₆F₅ H H H C₆F₅ H H ²⁾ H′-308 Ph HC₆F₅ H H H H C₆F₅ H ²⁾ H′-309 Ph H H C₆F₅ H H C₆F₅ H H ²⁾ H′-310 Ph H HC₆F₅ H H H C₆F₅ H ²⁾ H′-311 Ph H H OCH₃ H F H F H ²⁾ H′-312 Ph H H OCH₃H F CN F H ²⁾ H′-313 Ph H H OCH₃ H CF₃ H CF₃ H ²⁾ H′-314 Ph H H N(CH₃)₂H F H F H ²⁾ H′-315 Ph H H N(CH₃)₂ H F CN F H ²⁾ H′-316 Ph H H N(CH₃)₂ HCF₃ H CF₃ H ²⁾ H′-317 Ph ¹⁾ ¹⁾ H H H H H H ²⁾ H′-318 Ph ¹⁾ ¹⁾ H H H HCH₃ H ²⁾ H′-319 Ph ¹⁾ ¹⁾ H H H H OCH₃ H ²⁾ H′-320 Ph ¹⁾ ¹⁾ H H H HN(CH₃)₂ H ²⁾ H′-321 Ph ¹⁾ ¹⁾ H H H CH₃ H H ²⁾ H′-322 Ph ¹⁾ ¹⁾ H H H OCH₃H H ²⁾ H′-323 Ph ¹⁾ ¹⁾ H H H N(CH₃)₂ H H ²⁾ H′-324 Ph H H ¹⁾ ¹⁾ H H H H²⁾ H′-325 Ph H H ¹⁾ ¹⁾ H H CH₃ H ²⁾ H′-326 Ph H H ¹⁾ ¹⁾ H H OCH₃ H ²⁾H′-327 Ph H H ¹⁾ ¹⁾ H H N(CH₃)₂ H ²⁾ H′-328 Ph H H ¹⁾ ¹⁾ H CH₃ H H ²⁾H′-329 Ph H H ¹⁾ ¹⁾ H OCH₃ H H ²⁾ H′-330 Ph H H ¹⁾ ¹⁾ H N(CH₃)₂ H H ²⁾

²⁾ 4-C₆H₄C(CH)₃;

Cpd. R⁵ R⁶ R⁷ R⁸ R⁹ A¹⁰ A¹¹ A¹² A¹³ Z¹ = Z² I-1 Ph H H H H H H H H H I-2Ph H H H H H H CH₃ H H I-3 Ph H H H H H H Ph H H I-4 Ph H H H H H H t-BuH H I-5 Ph H H H H H H C₆H₁₁ H H I-6 Ph H H H H H H F H H I-7 Ph H H H HH H OCH₃ H H I-8 Ph H H H H H H OC₆H₅ H H I-9 Ph H H H H H H OH H H I-10Ph H H H H H H OCF₃ H H I-11 Ph H H H H H H OSi(CH₃)₂C(CH₃)₃ H H I-12 PhH H H H H H CF₃ H H I-13 Ph H H H H H H SCH₃ H H I-14 Ph H H H H H HSO₂CH₃ H H I-15 Ph H H H H H H SOCH₃ H H I-16 Ph H H H H H H SH H H I-17Ph H H H H H H NO₂ H H I-18 Ph H H H H H H N(CH₃)₂ H H I-19 Ph H H H H HH NH₂ H H I-20 Ph H H H H H H NCOCH₃ H H I-21 Ph H H H H H H NSO₂CH₃ H HI-22 Ph H H H H H H HNCH₂CH₃ H H I-23 Ph H H H H H H CHO H H I-24 Ph H HH H H H CH₂OH H H I-25 Ph H H H H H H CH₂Br H H I-26 Ph H H H H H HCH₂CN H H I-27 Ph H H H H H H CH₂CO₂H H H I-28 Ph H H H H H H CH₂OCH₃ HH I-29 Ph H H H H H H CH₂N(CH₂CH₃)₂ H H I-30 Ph H H H H H H CHCHCO₂CH₃ HH I-31 Ph H H H H H H CH₂CH₂CO₂CH₃ H H I-32 Ph H H H H H H C₆F₅ H H I-33Ph H H H H H H H CH₃ H I-34 Ph H H H H H CH₃ H H H I-35 Ph H H H H H H HCHCH₂ H I-36 Ph H H H H H CHCH₂ H H H I-37 Ph H H H H H H H Ph H I-38 PhH H H H H Ph H H H I-39 Ph H H H H H C₆F₅ H H H I-40 Ph H H H H H CF₃ HCF₃ H I-41 Ph H H H H H H H CF₃ H I-42 Ph H H H H H CF₃ H H H I-43 Ph HH H H H F H H H I-44 Ph H H H H H H H F H I-45 Ph H H H H H F H F H I-46Ph H H H H H H H OCF₃ H I-47 Ph H H H H H OCF₃ H H H I-48 Ph H H H H HNO₂ H CF₃ H I-49 Ph H H H H H CF₃ H NO₂ H I-50 Ph H H H H H CN H H HI-51 Ph H H H H H H H CN H I-52 Ph H H H H H H H Si(CH₃)₃ H I-53 Ph H HH H H Si(CH₃)₃ H H H I-54 Ph H H H H H NO₂ H CN H I-55 Ph H H H H H CN HNO₂ H I-56 Ph CF₃ H H H H H H H H I-57 Ph Cl H H H H H H H H I-58 Ph NO₂H H H H H H H H I-59 Ph CN H H H H H H H H I-60 Ph CH₃ H H H H H H H HI-61 Ph OCH₃ H H H H H H H H I-62 Ph Ph H H H H H H H H I-63 Ph F H H HH H H H H I-64 Ph H H H CF₃ H H H H H I-65 Ph H H H CN H H H H H I-66 PhH H H NO₂ H H H H H I-67 Ph H H H CH₃ H H H H H I-68 Ph H H H Ph H H H HH I-69 Ph H H H F H H H H H I-70 Ph H H H OCH₃ H H H H H I-71 Ph H H CF₃H H H H H H I-72 Ph H H CH₃ H H H H H H I-73 Ph H CF₃ H H H H H H H I-74Ph H CH₃ H H H H H H H I-75 Ph H F H H H H H H H I-76 Ph H C₆F₅ H H H HH H H I-77 Ph H H C₆F₅ H H H H H H I-78 Ph H C₆H₅ H H H H H H H I-79 PhH H C₆H₅ H H H H H H I-80 Ph H H OCH₃ H F H F H H I-81 Ph H CF₃ H H H HF H H I-82 Ph H H ¹⁾ ¹⁾ H H H H H I-83 Ph H H H H H Si(CH₃)₂C₆F₁₃ H H HI-84 CH₃ H H H H H H H H H I-85 Ph H C₆F₅ H H H H F H H I-86 Ph H C₆F₅ HH H H CF₃ H H I-87 Ph H C₆F₅ H H H C₆F₅ H H H I-88 Ph H C₆F₅ H H H HC₆F₅ H H I-89 Ph H H C₆F₅ H H C₆F₅ H H H I-90 Ph H H C₆F₅ H H H C₆F₅ H HI-91 Ph H H OCH₃ H F H F H H I-92 Ph H H OCH₃ H F CN F H H I-93 Ph H HOCH₃ H CF₃ H CF₃ H H I-94 Ph H H. N(CH₃)₂ H F H F H H I-95 Ph H HN(CH₃)₂ H F CN F H H I-96 Ph H H N(CH₃)₂ H CF₃ H CF₃ H H I-97 Ph ¹⁾ ¹⁾ HH H H H H H I-98 Ph ¹⁾ ¹⁾ H H H H CH₃ H H I-99 Ph ¹⁾ ¹⁾ H H H H OCH₃ H HI-100 Ph ¹⁾ ¹⁾ H H H H N(CH₃)₂ H H I-101 Ph ¹⁾ ¹⁾ H H H CH₃ H H H I-102Ph ¹⁾ ¹⁾ H H H OCH₃ H H H I-103 Ph ¹⁾ ¹⁾ H H H N(CH₃)₂ H H H I-104 Ph HH ¹⁾ ¹⁾ H H H H H I-105 Ph H H ¹⁾ ¹⁾ H H CH₃ H H I-106 Ph H H ¹⁾ ¹⁾ H HOCH₃ H H I-107 Ph H H ¹⁾ ¹⁾ H H N(CH₃)₂ H H I-108 Ph H H ¹⁾ ¹⁾ H CH₃ H HH I-109 Ph H H ¹⁾ ¹⁾ H OCH₃ H H H I-110 Ph H H ¹⁾ ¹⁾ H N(CH₃)₂ H H H

Cpd. R⁵ R⁶ R⁷ R⁸ R⁹ A¹⁰ A¹¹ A¹² A¹³ ²⁾ J-1 Ph H H H H H H H H H J-2 Ph HH H H H H CH₃ H H J-3 Ph H H H H H H Ph H H J-4 Ph H H H H H H t-Bu H HJ-5 Ph H H H H H H C₆H₁₁ H H J-6 Ph H H H H H H F H H J-7 Ph H H H H H HOCH₃ H H J-8 Ph H H H H H H OC₆H₅ H H J-9 Ph H H H H H H OH H H J-10 PhH H H H H H OCF₃ H H J-11 Ph H H H H H H OSi(CH₃)₂C(CH₃)₃ H H J-12 Ph HH H H H H CF₃ H H J-13 Ph H H H H H H SCH₃ H H J-14 Ph H H H H H HSO₂CH₃ H H J-15 Ph H H H H H H SOCH₃ H H J-16 Ph H H H H H H SH H H J-17Ph H H H H H H NO₂ H H J-18 Ph H H H H H H N(CH₃)₂ H H J-19 Ph H H H H HH NH₂ H H J-20 Ph H H H H H H NCOCH₃ H H J-21 Ph H H H H H H NSO₂CH₃ H HJ-22 Ph H H H H H H HNCH₂CH₃ H H J-23 Ph H H H H H H CHO H H J-24 Ph H HH H H H CH₂OH H H J-25 Ph H H H H H H CH₂Br H H J-26 Ph H H H H H HCH₂CN H H J-27 Ph H H H H H H CH₂CO₂H H H J-28 Ph H H H H H H CH₂OCH₃ HH J-29 Ph H H H H H H CH₂N(CH₂CH₃)₂ H H J-30 Ph H H H H H H CHCHCO₂CH₃ HH J-31 Ph H H H H H H CH₂CH₂CO₂CH₃ H H J-32 Ph H H H H H H C₆F₅ H H J-33Ph H H H H H H H CH₃ H J-34 Ph H H H H H CH₃ H H H J-35 Ph H H H H H H HCHCH₂ H J-36 Ph H H H H H CHCH₂ H H H J-37 Ph H H H H H H H Ph H J-38 PhH H H H H Ph H H H J-39 Ph H H H H H C₆F₅ H H H J-40 Ph H H H H H CF₃ HCF₃ H J-41 Ph H H H H H H H CF₃ H J-42 Ph H H H H H CF₃ H H H J-43 Ph HH H H H F H H H J-44 Ph H H H H H H H F H J-45 Ph H H H H H F H F H J-46Ph H H H H H H H OCF₃ H J-47 Ph H H H H H OCF₃ H H H J-48 Ph H H H H HNO₂ H CF₃ H J-49 Ph H H H H H CF₃ H NO₂ H J-50 Ph H H H H H CN H H HJ-51 Ph H H H H H H H CN H J-52 Ph H H H H H H H Si(CH₃)₃ H J-53 Ph H HH H H Si(CH₃)₃ H H H J-54 Ph H H H H H NO₂ H CN H J-55 Ph H H H H H CN HNO₂ H J-56 Ph CF₃ H H H H H H H H J-57 Ph Cl H H H H H H H H J-58 Ph NO₂H H H H H H H H J-59 Ph CN H H H H H H H H J-60 Ph CH₃ H H H H H H H HJ-61 Ph OCH₃ H H H H H H H H J-62 Ph Ph H H H H H H H H J-63 Ph F H H HH H H H H J-64 Ph H H H CF₃ H H H H H J-65 Ph H H H CN H H H H H J-66 PhH H H NO₂ H H H H H J-67 Ph H H H CH₃ H H H H H J-68 Ph H H H Ph H H H HH J-69 Ph H H H F H H H H H J-70 Ph H H H OCH₃ H H H H H J-71 Ph H H CF₃H H H H H H J-72 Ph H H CH₃ H H H H H H J-73 Ph H CF₃ H H H H H H H J-74Ph H CH₃ H H H H H H H J-75 Ph H F H H H H H H H J-76 Ph H C₆F₅ H H H HH H H J-77 Ph H H C₆F₅ H H H H H H J-78 Ph H C₆H₅ H H H H H H H J-79 PhH H C₆H₅ H H H H H H J-80 Ph H H OCH₃ H F H F H H J-81 Ph H CF₃ H H H HF H H J-82 Ph H H ¹⁾ ¹⁾ H H H H H J-83 Ph H H H H H Si(CH₃)₂C₆F₁₃ H H HJ-84 CH₃ H H H H H H H H H J-85 Ph H C₆F₅ H H H H F H H J-86 Ph H C₆F₅ HH H H CF₃ H H J-87 Ph H C₆F₅ H H H C₆F₅ H H H J-88 Ph H C₆F₅ H H H HC₆F₅ H H J-89 Ph H H C₆F₅ H H C₆F₅ H H H J-90 Ph H H C₆F₅ H H H C₆F₅ H HJ-91 Ph H H OCH₃ H F H F H H J-92 Ph H H OCH₃ H F CN F H H J-93 Ph H HOCH₃ H CF₃ H CF₃ H H J-94 Ph H H N(CH₃)₂ H F H F H H J-95 Ph H H N(CH₃)₂H F CN F H H J-96 Ph H H N(CH₃)₂ H CF₃ H CF₃ H H J-97 Ph ¹⁾ ¹⁾ H H H H HH H J-98 Ph ¹⁾ ¹⁾ H H H H CH₃ H H J-99 Ph ¹⁾ ¹⁾ H H H H OCH₃ H H J-100Ph ¹⁾ ¹⁾ H H H H N(CH₃)₂ H H J-101 Ph ¹⁾ ¹⁾ H H H CH₃ H H H J-102 Ph ¹⁾¹⁾ H H H OCH₃ H H H J-103 Ph ¹⁾ ¹⁾ H H H N(CH₃)₂ H H H J-104 Ph H H ¹⁾¹⁾ H H H H H J-105 Ph H H ¹⁾ ¹⁾ H H CH₃ H H J-106 Ph H H ¹⁾ ¹⁾ H H OCH₃H H J-107 Ph H H ¹⁾ ¹⁾ H H N(CH₃)₂ H H J-108 Ph H H ¹⁾ ¹⁾ H CH₃ H H HJ-109 Ph H H ¹⁾ ¹⁾ H OCH₃ H H H J-110 Ph H H ¹⁾ ¹⁾ H N(CH₃)₂ H H H

Z¹ = Z² = Z³ = Z⁴;

Cpd. R¹ R² R³ R⁴ R⁵ Z¹ K-1 H H H H Ph Ph K-2 H NO₂ H H Ph Ph K-3 H CH₃ HH Ph Ph K-4 H C(CH₃)₃ H H Ph Ph K-5 H CH(CH₃)₂ H H Ph Ph K-6 H CF₃ H HPh Ph K-7 H OCF₃ H H Ph Ph K-8 H F H H Ph Ph K-9 H OCH₃ H H Ph Ph K-10 HOPh H H Ph Ph K-11 H CN H H Ph Ph K-12 H SCH₃ H H Ph Ph K-13 H CO₂CH₃ HH Ph Ph K-14 H SO₂CH₃ H H Ph Ph K-15 H C₆H₄CF₃ H H Ph Ph K-16 CH₃ H H HPh Ph K-17 F H H H Ph Ph K-18 CF₃ H H H Ph Ph K-19 C(CH₃)₃ H H H Ph PhK-20 CN H H H Ph Ph K-21 NO₂ H H H Ph Ph K-22 OCH₃ H H H Ph Ph K-23 H HCH₃ H Ph Ph K-24 H H F H Ph Ph K-25 H H CF₃ H Ph Ph K-26 H H OCF₃ H PhPh K-27 H H CN H Ph Ph K-28 H H NO₂ H Ph Ph K-29 H H OCH₃ H Ph Ph K-30 HH SCH₃ H Ph Ph K-31 H H H H Ph CF₃ K-32 H NO₂ H H Ph CF₃ K-33 H CH₃ H HPh CF₃ K-34 H C(CH₃)₃ H H Ph CF₃ K-35 H CH(CH₃)₂ H H Ph CF₃ K-36 H CF₃ HH Ph CF₃ K-37 H OCF₃ H H Ph CF₃ K-38 H F H H Ph CF₃ K-39 H OCH₃ H H PhCF₃ K-40 H OPh H H Ph CF₃ K-41 H CN H H Ph CF₃ K-42 H SCH₃ H H Ph CF₃K-43 H CO₂CH₃ H H Ph CF₃ K-44 H SO₂CH₃ H H Ph CF₃ K-45 CH₃ H H H Ph CF₃K-46 F H H H Ph CF₃ K-47 CF₃ H H H Ph CF₃ K-48 C(CH₃)₃ H H H Ph CF₃ K-49CN H H H Ph CF₃ K-50 NO₂ H H H Ph CF₃ K-51 OCH₃ H H H Ph CF₃ K-52 H HCH₃ H Ph CF₃ K-53 H H F H Ph CF₃ K-54 H H CF₃ H Ph CF₃ K-55 H H OCF₃ HPh CF₃ K-56 H H CN H Ph CF₃ K-57 H H NO₂ H Ph CF₃ K-58 H H OCH₃ H Ph CF₃K-59 H H SCH₃ H Ph CF₃ K-60 H C₆H₄CF₃ H H Ph CF₃ K-61 H H H H Ph ¹⁾ K-62H NO₂ H H Ph ¹⁾ K-63 H CH₃ H H Ph ¹⁾ K-64 H C(CH₃)₃ H H Ph ¹⁾ K-65 HCH(CH₃)₂ H H Ph ¹⁾ K-66 H CF₃ H H Ph ¹⁾ K-67 H OCF₃ H H Ph ¹⁾ K-68 H F HH Ph ¹⁾ K-69 H OCH₃ H H Ph ¹⁾ K-70 H OPh H H Ph ¹⁾ K-71 H CN H H Ph ¹⁾K-72 H SCH₃ H H Ph ¹⁾ K-73 H CO₂CH₃ H H Ph ¹⁾ K-74 H SO₂CH₃ H H Ph ¹⁾K-75 CH₃ H H H Ph ¹⁾ K-76 F H H H Ph ¹⁾ K-77 CF₃ H H H Ph ¹⁾ K-78C(CH₃)₃ H H H Ph ¹⁾ K-79 CN H H H Ph ¹⁾ K-80 NO₂ H H H Ph ¹⁾ K-81 OCH₃ HH H Ph ¹⁾ K-82 H H CH₃ H Ph ¹⁾ K-83 H H F H Ph ¹⁾ K-84 H H CF₃ H Ph ¹⁾K-85 H H OCF₃ H Ph ¹⁾ K-86 H H CN H Ph ¹⁾ K-87 H H NO₂ H Ph ¹⁾ K-88 H HOCH₃ H Ph ¹⁾ K-89 H H SCH₃ H Ph ¹⁾ K-90 H C₆H₄CF₃ H H Ph ¹⁾ ¹⁾4-C₆H₄C(CH)₃;

Cpd. R¹ R² R³ R⁴ R⁵ Z¹ K′-1 H H H H Ph Ph K′-2 H NO₂ H H Ph Ph K′-3 HCH₃ H H Ph Ph K′-4 H C(CH₃)₃ H H Ph Ph K′-5 H CH(CH₃)₂ H H Ph Ph K′-6 HCF₃ H H Ph Ph K′-7 H OCF₃ H H Ph Ph K′-8 H F H H Ph Ph K′-9 H OCH₃ H HPh Ph K′-10 H OPh H H Ph Ph K′-11 H CN H H Ph Ph K′-12 H SCH₃ H H Ph PhK′-13 H CO₂CH₃ H H Ph Ph K′-14 H SO₂CH₃ H H Ph Ph K′-15 H C₆H₄CF₃ H H PhPh K′-16 CH₃ H H H Ph Ph K′-17 F H H H Ph Ph K′-18 CF₃ H H H Ph Ph K′-19C(CH₃)₃ H H H Ph Ph K′-20 CN H H H Ph Ph K′-21 NO₂ H H H Ph Ph K′-22OCH₃ H H H Ph Ph K′-23 H H CH₃ H Ph Ph K′-24 H H F H Ph Ph K′-25 H H CF₃H Ph Ph K′-26 H H OCF₃ H Ph Ph K′-27 H H CN H Ph Ph K′-28 H H NO₂ H PhPh K′-29 H H OCH₃ H Ph Ph K′-30 H H SCH₃ H Ph Ph K′-31 H H H H Ph CF₃K′-32 H NO₂ H H Ph CF₃ K′-33 H CH₃ H H Ph CF₃ K′-34 H C(CH₃)₃ H H Ph CF₃K′-35 H CH(CH₃)₂ H H Ph CF₃ K′-36 H CF₃ H H Ph CF₃ K′-37 H OCF₃ H H PhCF₃ K′-38 H F H H Ph CF₃ K′-39 H OCH₃ H H Ph CF₃ K′-40 H OPh H H Ph CF₃K′-41 H CN H H Ph CF₃ K′-42 H SCH₃ H H Ph CF₃ K′-43 H CO₂CH₃ H H Ph CF₃K′-44 H SO₂CH₃ H H Ph CF₃ K′-45 CH₃ H H H Ph CF₃ K′-46 F H H H Ph CF₃K′-47 CF₃ H H H Ph CF₃ K′-48 C(CH₃)₃ H H H Ph CF₃ K′-49 CN H H H Ph CF₃K′-50 NO₂ H H H Ph CF₃ K′-51 OCH₃ H H H Ph CF₃ K′-52 H H CH₃ H Ph CF₃K′-53 H H F H Ph CF₃ K′-54 H H CF₃ H Ph CF₃ K′-55 H H OCF₃ H Ph CF₃K′-56 H H CN H Ph CF₃ K′-57 H H NO₂ H Ph CF₃ K′-58 H H OCH₃ H Ph CF₃K′-59 H H SCH₃ H Ph CF₃ K′-60 H C₆H₄CF₃ H H Ph CF₃ K′-61 H H H H Ph ¹⁾K′-62 H NO₂ H H Ph ¹⁾ K′-63 H CH₃ H H Ph ¹⁾ K′-64 H C(CH₃)₃ H H Ph ¹⁾K′-65 H CH(CH₃)₂ H H Ph ¹⁾ K′-66 H CF₃ H H Ph ¹⁾ K′-67 H OCF₃ H H Ph ¹⁾K′-68 H F H H Ph ¹⁾ K′-69 H OCH₃ H H Ph ¹⁾ K′-70 H OPh H H Ph ¹⁾ K′-71 HCN H H Ph ¹⁾ K′-72 H SCH₃ H H Ph ¹⁾ K′-73 H CO₂CH₃ H H Ph ¹⁾ K′-74 HSO₂CH₃ H H Ph ¹⁾ K′-75 CH3 H H H Ph ¹⁾ K′-76 F H H H Ph ¹⁾ K′-77 CF3 H HH Ph ¹⁾ K′-78 C(CH3)3 H H H Ph ¹⁾ K′-79 CN H H H Ph ¹⁾ K′-80 NO2 H H HPh ¹⁾ K′-81 OCH3 H H H Ph ¹⁾ K′-82 H H CH₃ H Ph ¹⁾ K′-83 H H F H Ph ¹⁾K′-84 H H CF₃ H Ph ¹⁾ K′-85 H H OCF₃ H Ph ¹⁾ K′-86 H H CN H Ph ¹⁾ K′-87H H NO₂ H Ph ¹⁾ K′-88 H H OCH₃ H Ph ¹⁾ K′-89 H H SCH₃ H Ph ¹⁾ K′-90 HC₆H₄CF₃ H H Ph ¹⁾ ¹⁾ 4-C₆H₄C(CH)₃;

Cpd . R¹ R² R³ R⁴ R⁵ Z¹ = Z² L-1 H H H H Ph H L-2 H NO₂ H H Ph H L-3 HCH₃ H H Ph H L-4 H C(CH₃)₃ H H Ph H L-5 H CH(CH₃)₂ H H Ph H L-6 H CF₃ HH Ph H L-7 H OCF₃ H H Ph H L-8 H F H H Ph H L-9 H OCH₃ H H Ph H L-10 HOPh H H Ph H L-11 H CN H H Ph H L-12 H SCH₃ H H Ph H L-13 H CO₂CH₃ H HPh H L-14 H SO₂CH₃ H H Ph H L-15 CH₃ H H H Ph H L-16 F H H H Ph H L-17CF₃ H H H Ph H L-18 C(CH₃)₃ H H H Ph H L-19 CN H H H Ph H L-20 NO₂ H H HPh H L-21 OCH₃ H H H Ph H L-22 H H CH₃ H Ph H L-23 H H F H Ph H L-24 H HCF₃ H Ph H L-25 H H OCF₃ H Ph H L-26 H H CN H Ph H L-27 H H NO₂ H Ph HL-28 H H OCH₃ H Ph H L-29 H H SCH₃ H Ph H L-30 H C₆H₄CF₃ H H Ph H

Cpd. R¹ R² R³ R⁴ R⁵ ¹⁾ M-1 H H H H Ph H M-2 H NO₂ H H Ph H M-3 H CH₃ H HPh H M-4 H C(CH₃)₃ H H Ph H M-5 H CH(CH₃)₂ H H Ph H M-6 H CF₃ H H Ph HM-7 H OCF₃ H H Ph H M-8 H F H H Ph H M-9 H OCH₃ H H Ph H M-10 H OPh H HPh H M-11 H CN H H Ph H M-12 H SCH₃ H H Ph H M-13 H CO₂CH₃ H H Ph H M-14H SO₂CH₃ H H Ph H M-15 CH₃ H H H Ph H M-16 F H H H Ph H M-17 CF₃ H H HPh H M-18 C(CH₃)₃ H H H Ph H M-19 CN H H H Ph H M-20 NO₂ H H H Ph H M-21OCH₃ H H H Ph H M-22 H H CH₃ H Ph H M-23 H H F H Ph H M-24 H H CF₃ H PhH M-25 H H OCF₃ H Ph H M-26 H H CN H Ph H M-27 H H NO₂ H Ph H M-28 H HOCH₃ H Ph H M-29 H H SCH₃ H Ph H M-30 H C₆H₄CF₃ H H Ph H ¹⁾ Z¹ = Z² = Z³= Z⁴;


10. An organic electronic device, comprising an emitting layer whereinthe emitting layer comprises a compound according to claim
 9. 11. Anorganic electronic device according to claim 10 which is an organiclight emitting diode.
 12. A device selected from the group consisting ofstationary or mobile displays, mobile phones, laptops, pdas, TV sets,displays in printers, kitchen equipment, billboards, lightings andinformation or destination boards in trains or buses, containing anorganic light emitting diode according to claims
 11. 13. The device ofclaim 10, further comprising a hole transport layer selected from thegroup consisting of polyvinyl-carbazol,N,N′-diphenyl-N,N′-bis(3-methylphenyl)-[1,1′-biphenyl]-4,4′-diamine(TPD), 1,1-bis[(di-4-tolylamino)phenyl]cyclohexane (TAPC),N,N′-bis(4-methylphenyl)-N,N′-bis(4-ethylphenyl)-[1,1′-(3,3′-dimethyl)biphenyl]4,4′-diamine(ETPD), tetrakis-(3-methylphenyl)-N,N,N′,N′-2,5-phenylenediamine (PDA),a-phenyl-4-N,N-diphenylaminostyrene (TPS),p-(diethylamino)benzaldehydediphenylhydrazone (DEH), triphenylamine(TPA), bis[4-(N,N-diethylamino)-2-methylphenyl](4-methylphenyl)methane(MPMP),1-phenyl-3-[p-(diethylamino)styryl]-5-[p-(diethylamino)phenyl]pyrazoline(PPR or DEASP), 1,2-trans-bis(9H-carbazol-9-yl)cyclobutane (DCZB),N,N,N′,N′-tetrakis (4-methylphenyl)-(1,1′-biphenyl)-4,4′-diamine (TTB),4,4′-N,N-dicarbazole-biphenyl (CBP),N,N-dicarbazoyl-1,4-dimethene-benzene (DCB), porphyrinic compounds andcombinations thereof.
 14. An organic electronic device, comprising anemitting layer wherein the emitting layer comprises a compound accordingto claim
 1. 15. The device of claim 14, further comprising a holetransport layer selected from the group consisting ofpolyvinyl-carbazol,N,N′-diphenyl-N,N′-bis(3-methylphenyl)-[1,1′-biphenyl]-4,4′-diamine(TPD), 1,1-bis[(di-4-tolylamino)phenyl]cyclohexane (TAPC),N,N′-bis(4-methylphenyl)-N,N′-bis(4-ethylphenyl)-[1,1′-(3,3′-dimethyl)biphenyl]4,4′-diamine(ETPD), tetrakis-(3-methylphenyl)-N,N,N′,N′-2,5-phenylenediamine (PDA),a-phenyl-4-N,N-diphenylaminostyrene (TPS),p-(diethylamino)benzaldehydediphenylhydrazone (DEH), triphenylamine(TPA), bis[4-(N,N-diethylamino)-2-methylphenyl](4-methylphenyl)methane(MPMP),1-phenyl-3-[p-(diethylamino)styryl]-5-[p-(diethylamino)phenyl]pyrazoline(PPR or DEASP), 1,2-trans-bis(9H-carbazol-9-yl)cyclobutane (DCZB),N,N,N′,N′-tetrakis(4-methylphenyl)-(1,1′-biphenyl)-4,4′-diamine (TTB),4,4′-N,N-dicarbazole-biphenyl (CBP),N,N-dicarbazoyl-1,4-dimethene-benzene (DCB), porphyrinic compounds andcombinations thereof.
 16. A device selected from the group consisting ofstationary or mobile displays, mobile phones, laptops, pdas, TV sets,displays in printers, kitchen equipment, billboards, lightings andinformation or destination boards in trains or buses, containing as anorganic electronic device an organic light emitting diode according toclaim
 15. 17. A device selected from the group consisting of stationaryor mobile displays, mobile phones, laptops, pdas, TV sets, displays inprinters, kitchen equipment, billboards, lightings and information ordestination boards in trains or buses, containing as an organicelectronic device an organic light emitting diode according to claim 14.18. An organic electronic device according to claim 14 which is aorganic light emitting diode.